Synthesis of 5,6-dideoxy-5-phenylphosphinyl-L-galactopyranoses. The P-in-ring sugar analogs of L-fucose.
スポンサーリンク
概要
- 論文の詳細を見る
1,2-<I>O</I>-Isopropylidene-3-<I>O</I>-methyl-6-<I>O</I>-tosyl-β-D-<I>arabino</I>-hexofuranos-5-ulose (<B>9a</B>) and its 3-<I>O</I>-benzyl congener (<B>9b</B>) were prepared from 1,2:5,6-di-<I>O</I>-isopropylidene-β-D-altrofuranose in 4 steps. Addition of methyl phenylphosphinate to <B>9a</B> and <B>9b</B> in the presence of DBU, followed by reduction with Raney Ni, afforded (5<I>R</I> and 5<I>S</I>)-5,6-dideoxy-1,2-<I>O</I>-isopropylidene-5-[(methoxy)phenylphosphinyl]-3-<I>O</I>-methyl-β-D-<I>arabino</I>-hexofuranose(<B>11a</B>) and 3-<I>O</I>-benzyl congener (<B>11b</B>), respectively. The latter compound (<B>11b</B>) was debenzylated to 3-<I>O</I>-unsubstituted hexofuranose <B>11d</B>. By reduction with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by acid hydrolysis, these key intermediates <B>11a</B>, <B>11b</B>, and <B>11d</B> provided the title L-fucoses <B>13</B> (together with a minor proportion of D-altropyranoses <B>14</B>) having as phenylphosphinylidene group in place of the ring oxygen. Compounds <B>13</B> and <B>14</B> were converted into per-<I>O</I>-acetyl derivatives for structural and conformational analysis by spectroscopy.
- 公益社団法人 日本化学会の論文
著者
-
HANAYA Tadashi
Department of Chemistry, Faculty of Science, Okayama University
-
Hanaya Tadashi
Department Of Chemistry Faculty Of Science Okayama University
-
Yamamoto Hiroshi
Departmemt Of Chemical Engineering University Of Tokyo
-
Kawamoto Heizan
Department Of Chemistry Faculty Of Science Okayama University
-
Hogg Alan
Department of Chemistry, University of Alberta
-
Ohmae Takeshi
Department of Chemistry, Faculty of Science, Okayama University
-
Armour Margaret-Ann
Department of Chemistry, University of Alberta
関連論文
- Metamorphic history and tectonic evolution of the Himalayan UHP eclogites in Kaghan valley, Pakistan
- Micellization Protocols for Amphiphilic Polyelectrolytes in Water. How Do Polymers Undergo Intrapolymer Associations?
- Self-Association of Dodecyl Moieties Covalently Linked to a Polyelectrolyte in a Small Amount
- Partial Spontaneous Regression of Hepatocellular Carcinoma: A Case with High Concentrations of Serum Lens Culinaris Agglutinin-reactive Alpha Fetoprotein
- Characterization of Chondroitin/Dermatan Sulfate Proteoglycans Synthesized by Bovine Retinal Pericytes in Culture(Highlighted paper selected by Editor-in-chief)(Biochemistry/Molecular Biology)
- Selective Increase in Decorin Core mRNA Level in Cultured Vascular Smooth Muscle Cells after Exposure to Advanced Glycation Endproducts
- Induction of Decorin Core Protein Synthesis by Advanced Glycation Endproducts in Cultured Vascular Smooth Muscle Cells(PROCEEDINGS OF 24TH SYMPOSIUM ON TOXICOLOGY AND ENVIRONMENTAL HEALTH)
- Effects of unipedal standing balance exercise on the prevention of falls and hip fracture among clinically defined high-risk elderly individuals : a randomized controlled trial
- Report on the Japanese Orthopaedic Association's 3-year project observing hip fractures at fixed-point hospitals
- X-ray Phase-Contrast Imaging and X-ray Absorption Fine Structure Analysis using Parametric X-ray Radiation Generated at LEBRA, Nihon University
- W-1-4-4 Prevention of a patient's falling by using a sensor-controlled ambulation support machine : Analysis of leg muscle action based on the musculo-skeletal model
- The Decay of ^Pr
- Renal cell carcinoma with unusual metastasis to the gallbladder
- Cortical Neurophysiological Modification after Peripheral Neuronal Sensitization
- Zeeman Effect of R-Lines in Alexandrite under High Magnetic Fields
- Anterior fissure of the right liver-the third door of the liver
- Resection of Liver Metastasis from Alpha-Fetoprotein-Producing Early Gastric Cancer: Report of a Case
- A Recursive Maximum Likelihood Decoding Algorithm for Some Transitive Invariant Binary Block Codes
- 194. Equilibrium Function in Abnormal Varieties of Posture,Especially in Scoliosis
- Reduced expression of endogenous secretory receptor for advanced glycation endproducts in hippocampal neurons of Alzheimer’s disease brains
- Development of sensitive high-performance liquid chromatography with fluorescence detection using 4-(4, 5-diphenyl-1H-imidazol-2-yl)-benzoly chloride as a labeling reagent for determination of bisphenol A in plasma samples
- A case of solitary intraductal papilloma of the breast coexisting with ductal carcinoma in situ (DCIS)
- Case Report* MR Appearance of Hemangiopericytoma of the Thigh
- Effect of Surface Treatment on Interfacial Strength between Bamboo Fiber and PP Resin(Green Composites)
- Self-Association in Water of Copolymers of Sodium 2-(Acrylamido)-2-methylpropanesulfonate and N-Oleylmethacrylamide Characterized by Fluorescence Quenching
- Identification of a New Isotope ^Tb
- Increased Neutrophils in Bronchoalveolar Lavage Fluids from a Patient with Pulmonary Edema Associated with Pheochromocytoma
- Mouse Mammary Tumor Virus Proviral Integration in the DD/Tbr Mice
- Beta-Decay Energies of ^,^,^Ba and ^,^Cs
- Level Scheme of ^Ba Fed by the ^La Decay
- The effect of trunk muscle exercises in patients over 40 years of age with chronic low back pain
- The Transcutaneous Electrical Nerve Stimulation Applied to Contralateral Limbs for the Phantom Limb Pain
- Mechanism of Cadmium Stimulation on the Production of Fibrinolytic Proteins in Vascular Endothelial Cells (Proceedings of the 23rd Symposium on Toxicology and Environmental Health)
- Sarcomatous hepatocellular carcinoma without previous anticancer therapy
- Effect of Nasal Continuous Positive Airway Pressure Treatment on Plasma Adrenomedullin Levels in Patients with Obstructive Sleep Apnea Syndrome : Roles of Nocturnal Hypoxia and Oxidant Stress
- Postprandial Hyperglycemia After a Gastrectomy and the Prediabetic State : A Comparison Between a Distal and Total Gastrectomy
- Beta Decay of ^Pr into Levels in ^Nd
- Low-Lying Levels in ^Nd in the Decay of ^Pr
- Decay of ^152Nd
- Half-Lives of Levels in ^Sr and ^Sr
- Aminopeptidase N/CD13 Regulates the Fetal Liver Microenvironment of Hematopoiesis(Miscellaneous)
- Up-regulation of IL-4 production by the activated cAMP/cAMP-dependent protein kinase (protein kinase A) pathway in CD3/CD28-stimulated naive T cells
- Roles of the Receptor for Advanced Glycation Endproducts in Diabetes-Induced Vascular Injury
- AGE and Endothelial Cells
- Crystal Structure of 2,5-Bis-(3,5-di-tert-butyl-benzyl)-3,6-bis-(4-dimethylamino-phenyl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione
- Immunohistochemical localization of serotonin transporter in normal and colchicine treated rat brain
- Molecular mechanisms underlying inflammatory lung diseases in the elderly : Development of a novel therapeutic strategy for acute lung injury and pulmonary fibrosis
- One Year Follow-Up of The First Bilateral Living-Donor Lobar Lung Transplantation in Japan
- Q_ Measurement of^La
- Atomic Scale Oxidation Process on Hydrogen-Terminated Silicon Surface
- Simultaneous live video presentation during knee arthroscopy
- Insufficient Resistance of Trehalose-6, 6'-Dimycolate-Treated T-Cell Receptor δ Gene Mutant (TCR δ^) Mice against Influenza Virus Infection
- Mechanical augmentation of the vertebral body by calcium phosphate cement injection
- Q_β Measurements of Neutron-Rich Isotopes in the Mass Region 147 ≤A≤152
- Syntheses of Chiral 4'-Hydroxy and 1',4'-Dihydroxy-γ-ionylideneacetic Acids, Fungal Biosynthetic Intermediates of Abscisic Acid(Organic Chemistry)
- Enzymatic Preparation of Chiral 4-Hydroxy-2,2-dimethyl-1-cyclohexanone as a Chiral Building Block(Organic Chemistry)
- Synthesis of (±)-4'-Hydroxy-γ-ionylideneacetic Acids, Fungal Biosynthetic Intermediates of Abscisic Acid(Organic Chemistry)
- Synthesis of (±)-(2Z,4E)-trans-1',4'-Dihydroxy-γ-ionylideneacetic Acid, a Fungal Biosynthetic Intermediate of Abscisic Acid(Organic Chemistry)
- Synthesis of Chiral 3'-Hydroxy-γ-ionylideneacetic Acids (Organic Chemistry)
- How to Quantize Fields Canonically on Discrete Space-Time : Particles and Fields
- Conserved Quantities of Field Theory on Discrete Spacetime
- Orientation Dependence of Lateral Solid-Phase-Epitaxial Growth in Amorphous Si Films
- On the Mechanisms of Lateral Solid Phase Epitaxial Growth of Amorphous Si Films Evaporated on SiO_2 Patterns
- Characterization of Solid-Phase Epitaxially-Grown Silicon Films on SiO_2
- Morphological study of the endotoxin translocation in the ileal epithelium of monkey
- ON THE DISTORITION OF CARDIAC ELECTRICAL SIGNALS DUE TO THE TRANSMISSION TO THE BODY SURFACE : Electrocardiography : IInd Auditorium : Proceedings of the 43rd Annual Meeting of the Japanese Circulation Society, Tokyo, 1979
- A Facile Preparation of 5-Isopropyl-idene-3,8-dimethyl-1(5H)-azulenone and Its Crystal Structure
- Preparation and Characteristic Properties of 1,4-Bis(3-guaiazulenylmethylium)benzene Bishexanuorophosphate
- Electrochemical Behavior of 5, 5'-Biguaiazulene-3, 3' (5H, 5'H) -dione and Its Four Unique Autoxidation Products
- Conjugation in Tetrahymena : Its Relation to Concanavalin A Receptor Distribution on the Cell Surface : Cell Biology
- Decay Study of ^La
- Decay of ^Pr Isomers to Levels of ^Nd
- Level Properties of ^Nd in the Decay of ^Pr
- Decay of ^Pm to Levels of ^Sm
- Decay of ^Ho Isomers to Levels in ^Er
- Decay of ^Dy to Levels of ^Ho
- Decay of ^Ho to Levels of ^Er
- (一般演題)(日本アフェレシス学会第22回関西地方会抄録)
- Relative Safety of Anterior Microsurgical Decompression Versus Laminoplasty for Cervical Myelopathy With a Massive Ossified Posterior Longitudinal Ligament
- Mechanical properties of the femur filled with calcium phosphate cement under torsional loading : a model in rabbits
- Peripheral Administration of Magnesium Sulfate and Ketamine Hydrochloride Produces Hypesthesia to Mechanical Stimuli in Humans
- Changes of wide dynamic range neuronal responses to mechanical cutaneous stimuli following acute compression of the rat sciatic nerve
- Edaravone Improves the Survival of Rats Subjected to Hemorrhagic Shock Without Resuscitation
- X-Ray Crystal Structure of Guaiazulenequinone and the Structures of Two New Guaiazulenone Derivatives^1
- Prostate cancer antigen-1 contributes to cell survival and invasion though discoidin receptor 1 in human prostate cancer
- Simulator for Measuring Elderly Visual Performances While Driving(Internationa Session 3)
- Multi-Excitation-Laser Raman Analysis of Chirality-Controlled Single-Walled Carbon Nanotubes with Free Electron Laser Irradiation during Growth
- X Chromosome Territories in Human Female Lymphocytes
- Adaptation of a preembedding electron microscopic in situ hybridization for detection of the telomere region in human interphase nuclei
- Effect of inhibition of glycogen synthase kinase-3 on cardiac hypertrophy during acute pressure overload
- Enhancement of pedicle screw stability using calcium phosphate cement in osteoporotic vertebrae : in vivo biomechanical study
- Novel Stereoselective Preparation and Conformational Analysis of Furanose-Type Phosphono Sugar C -Glycosides
- Preparation and Structure of Phosphono Sugar N-Glycosides
- PB197 SELECTIVE SYNTHESIS OF 5-DEOXY-5-C__--(ETHYLPHOSPHINYL) -D__=-GLUCO- AND L__=-IDOPYRANOSES
- Synthesis and reactions of 2-arylhydrazinotropones. II. Synthesis of 5-aryltropolones and B-ring-open colchicine analogues via benzidine type rearrangement of 2-(2-arylhydrazino)tropones.
- Synthesis of 5,6-dideoxy-5-phenylphosphinyl-L-galactopyranoses. The P-in-ring sugar analogs of L-fucose.
- Synthesis and structural analysis of 5-deoxy-5-((R)- and (S)-methylphosphinyl)-.ALPHA.,.BETA.-D-manno- and -L-gulopyranoses.
- Synthesis and structural analysis of 4-deoxy-4-(hydroxyphosphinyl and phenylphosphinyl)-D-ribofuranoses.
- A convenient synthesis of (2R)-1-amino-1-deoxy-1-phosphinylglycerols.
- A convenient synthesis of 1,2,4-tri-O-acetyl-5-deoxy-5-((R)-and (S)-ethylphosphino and phenylphosphino)-3-O-methyl-.ALPHA.,.BETA.-D-xylopyranoses and their phosphinothioyl derivatives.