Aminocyclitols. XXIX. Synthesis of Inosadiamines <I>via</I> 1,3-Biimino-1,3-dideoxy-inositols

スポンサーリンク

概要

• 論文の詳細を見る

• Hydrazinolysis of DL-1,4-dibromo-1,4-dideoxy-<I>chiro</I>-inositol (<B>3a</B>), followed by catalytic hydrogenation and acetylation, afforded di-<I>N</I>-acetyl-tetra-<I>O</I>-acetyl-<I>neo</I>-inosadiamine-1,3 (<B>6a</B>) and -<I>scyllo</I>-inosadiamine-1,3 (<B>7</B>) in 18% and 24% yields, respectively. From the intact hydrazinolyzate of <B>3a</B>, two new stereoisomeric 1,3-biimino-1,3-dideoxy-inositols (<B>4a</B> and <B>5a</B>) could be isolated, and their structures were established by correlating to the corresponding inosadiamines. A similar hydrazinolysis of 3,6-di-<I>O</I>-<I>p</I>-tolylsulfonyl-<I>muco</I>-inositol (<B>12</B>) gave sole crystalline 1,3-biimino compound (<B>13a</B>), whose structure was followed from its conversion into known di-<I>N</I>-acetyltetra-<I>O</I>-acetyl-<I>myo</I>-inosadiamine-4,6 (<B>14</B>). PMR spectra of four 1,3-biimino compounds were discussed.

• 公益社団法人 日本化学会の論文

著者

• Ogawa Seiichiro

  Department Of Applied Cemistry Faculty Of Science And Technology Keio University

• Suami Tetsuo

  Department of Applied Chemistry Faculty of Engineering Keio University

• Uchida Masaru

  Department of Applied Chemistry, Faculty of Engineering, Keio University

• Uchino Hayashi

  Department of Applied Chemistry, Faculty of Engineering, Keio University

関連論文

• Fibroblast screening for chaperone therapy in β-galactosidosis
• Total Synthesis and Trehalase-Inhibitory Activity of Trehalostatin and Its Diastereoisomer
• Total Synthesis of Trehalase Inhibitor, Trehazolin
• DETERMINATIONS OF PSEUDO-α-AND PSEUDO-β-GLUCOSE BY GASCHROMATOGRAPHY, HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY AND ENZYMIC COLORIMETRY
• Total Synthesis of Acanthacerebroside A and Astrocerebroside A via a Chiral Epoxide Intermediate Derived from _L-Quebrachitol
• Convenient Synthesis of Oxo-Linked 5a-Carba-di- and tri-saccharides of Biological Interests
• 生化学上興味あるカルバ糖質の設計と合成
• PB166 SYNTHETIC STUDIES ON (+)-ASTELTOXIN, A NOVEL MYCOTOXIN ISOLATED FROM ASPERGILLUS STELLATUS : STEREOSELECTIVE SYNTHESIS OF THE BIS (TETRAHYDROFURAN) MOIETY (C-1 TO C-9)
• Total Syntheses of PI-201 and Related Compounds
• A New, Convenient Cell-Based Screening Method for Small-Molecule Glycolytic Inhibitors
• Total Synthesis of Antibiotic (-)-Oudemansin X Utilizing L-Quebrachitol as a Chiral Pool
• The effect of N-octyl-β-valienamine on β-glucosidase activity in tissues of normal mice
• Studies on Antibiotics and Related Substances. XVII. Syntheses of trans-2-Aminocyclohexyl-D-glucosaminides
• The Synthesis and Configuration Analysis of 2-Amino-1,3-cyclohexanediol
• Synthesis of potential antineoplastic anthracenedione derivatives. I. Sugar derivatives.
• Synthesis of potential antineoplastic anthracenedione derivatives. II. 1,2-Dihydroxy derivatives.
• Nucleoside analogs. 4. Synthesis of 3'-amino-3'-deoxyadenosine analogs.
• Nucleoside analogs. 6. A synthesis of carbocyclic puromycin analogs.
• Nucleoside Analogs. II. A Synthesis of 9-Adenyl-deoxyinositols
• Synthesis on 1,4-diaminocyclitol antibiotics. IV. Synthesis of 7'-phenylfortimicin A and 7'-phenyl-6'-epifortimicin A.
• Synthetic approach toward antibiotic tunicamycins. II.
• Pseudo-sugars. VI. Synthesis of six isomers of 5-hydroxymethyl-1,2,3,4-cyclohexanetetrol (pseudo-hexopyranose) and their derivatives.
• Aminocyclitols. 36. Chlorination and dechlorination of aminocyclitol and inositol derivatives. Preparation of dideoxy- and trideoxystreptamines.
• Synthetic approach toward antibiotic ezomycins. II Synthesis of 5-amino-3,7-anhydro-5-deoxyoctofuranose-(1,4) derivatives.
• Total syntheses of (+)-altholactone[(+)-goniothalenol] and three stereocongeners and their cytotoxicity against several tumor cell lines.
• Pseudo-sugars. XVI Facile synthesis of pseudo-.ALPHA.-D and L-glucopyranoses.
• Chemical modification of neamine. 5. Preparation of amino-deoxyneamines.
• Synthesis of cytidine, uridine, and adenosine 5'-(2,6-diamino-2,6-dideoxy-.ALPHA.-D-glucopyranosyl diphosphates) (neosamine C-CDP, -UDP, and -ADP).
• Aminocyclitols. 34. Synthesis of inosadiamine-1,4 derivatives.
• Proton Magnetic Resonance Studies on Specifically Deuterated Sucrose Acetates
• Aminocyclitols. XXVIII. Bromination of Inosamines and Inosadiamines
• Pseudo-sugars. Part XXVI. Synthesis of some anhydro derivatives of dl-1-C-hydroxymethyl-1,2,3,4,5,6-cyclohexanehexol.
• Synthesis of Planteose
• Synthesis of pseudo-.BETA.-DL-galactopyranose and pseudo-.ALPHA.-DL-altropyranose.
• Inositol Derivatives. IV. Synthesis of Anhydro Derivatives of 1,2-O-Cyclohexylidene-inositol
• Inositol Derivatives. V. Selective Benzoylation of 1,2-O-Cyclohexylidene-myo-inositol and Preparation of New O-p-Tolylsulfonyl-myo-inositols
• Synthetic studies on the validamycins. XII. Synthesis of optically active valienamine and validatol.
• Synthetic approach toward antibiotic tunicamycins.
• Synthesis of stachyose tetradecaacetate and an isomer.
• Synthesis of (2-chloroethyl)-nitrosourea derivatives of carbohydrate.
• Studies of tritylated pentoses and 6-deoxyhexoses. II. Trityl ethers of methyl .ALPHA.- and .BETA.-L-rhamnopyranoside and their derivatives.
• Claisen rearrangements of 5,6-dideoxy-1,2-o-isopropylidene-.ALPHA.-D-xylo- and .ALPHA.-D-ribo-hept-5-eno-1,4-furanoses with triethyl orthoacetate.
• Syntheses of optically active pentaacetates of pseudo-.BETA.-L-allopyranose and pseudo-.ALPHA.-D-mannopyranose.
• Total synthesis of (.+-.)-zeylena.
• Conversion of .BETA.-senepoxide to crotepoxide : Total synthesis of (+)-crotepoxide.
• The synthesis of purpurosamine B derivatives.
• Synthesis on 1,4-diaminocyclitol antibiotics. II Synthesis of 7'-propylfortimicin A.
• New synthesis of penta-N,O-acetyl-DL-validamine and pseudo-2-amino-2-deoxy-.ALPHA.-DL-mannopyranose, and their uronate analogs.
• Synthetic studies on the validamycins. IX. Synthesis of some racemic isomers of validoxylamine A.
• Pseudo-sugars. XIV. Synthesis of sweet-tasting pseudo-.BETA.-DL-fructopyranose.
• Synthetic studies on the validamycins. II. Synthesis of 1L-1-O-(.BETA.-D-glucopyranosyl)-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol.
• Synthetic studies on the validamycins. III. Bromination of DL-tri-O-acetyl-(1,3/2)-4-methylene-5-cyclohexene-1,2,3-triol. Preparation of several branched-chain unsaturated cyclitols related to valienamine.
• Pseudo-sugars. 4. A facile synthesis of DL-validamine and its derivative.
• Pseudo-sugars. X. Synthesis of several branched-chain unsaturated cyclitols and their derivatives.
• Pseudo-sugars. VIII. Synthesis of DL-1-epivalidamine and related compounds.
• Synthesis and biological activities of 2-amino-2-deoxy- and 6-amino-6-deoxy-.ALPHA.-D-glucopyranosyl-2,5-dideoxystreptamines.
• Synthesis and epoxidation of trans-5,6-diacetoxy-1-benzoyloxymethyl-1,3-cyclohexadiene.
• Aminocyclitols. XXVI. A Synthesis of Aminocyclopentanetetrols
• Modification of aminocyclitol antibiotics. 6. Preparation of 5-deoxykanamycin B.
• Synthesis of Carbocydic Adenosine Analogs: 9-(2′,3′,4′,5′-Tetrahydroxycyclopentyl)adenines
• Construction of an optically active 7-oxabicyclo[4.3.0]non-4-en-3-one skeleton from D-glucose, and its transformation to some pseudo-hexopyranoses.
• Hydrazinolysis of Sugar Sulfonates
• A synthesis of (+)-cyclaradine, carbocyclic analogue of 9-.BETA.-D-arabinofuranosyladenine.
• Synthesis on 1,4-diaminocyclitol antibiotics. V Synthesis of 3'-enofortimicin D.
• Synthetic studies on the validamycins. I. Synthesis of .BETA.-D-glucopyranosylvalidamine: 1L-2-O-(.BETA.-D-Glucopyranosyl)-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol.
• Inositol derivatives. 10. Isopropylidenation of 1,2-O-cyclohexylidene-myo-inositol derivatives and preparation of unaccessible blocked inositols.
• Selective p-Toluenesulfonylation of myo-Inositol Derivatives
• Synthesis of mono-O-tritylraffinoses and deca-O-acetylraffinoses.
• Pseudo-sugars. 3. Alternative synthesis of penta-N,O-acetyl-DL-validamine and its analogs.
• Aminocyclitols. XXVII. Preparation of Deoxyinosamines from vibo-Quercitol
• Aminocyclitols. XXIX. Synthesis of Inosadiamines via 1,3-Biimino-1,3-dideoxy-inositols
• Aminocyclitols. XXIV. Synthesis of Inosamines from Bromodeoxyinositols
• p-Toluenesulfonylation of 1,2-O-Cyclohexylidene-myo-inositol
• Pseudo-sugars. 5. Synthesis of DL-validatol and DL-deoxyvalidatol, and their epimers.
• Inositol Derivatives. VI. Convenient Synthesis of DL-profo-Quercitol from myo-Inositol

もっと見る 閉じる

スポンサーリンク