Studies on Amino Sugars. I. Synthesis of 5-Amino-5-deoxyuronic Acid and 5-Amino-5-deoxysaccharic Acid Derivatives from D-Glucuronolactone
スポンサーリンク
概要
- 論文の詳細を見る
Synthesis of 5-amino-5-deoxyuronic acid and 5-amino-5-deoxysaccharic acid derivatives from D-glucuronolactone is described. 1,2-O-Isopropylidene-D-glucofuranurono-6,3-lactone (I) was oxidized to 5-ulose (II), sodium salt of which was derived to the oxime (IVb). Catalytic hydrogenation of IVb using Adams' catalyst gave crystalline 5-aminated 1,2-O-isopropylidene-hexuronic acid (V) consisting of D-gluco and L-ido isomers. N-Acetylation of V gave each isomer separated as crystals of 6,3-lactone. Acid hydrolysis of the isopropylidene group in 5-acylamino-5-deoxy-1,2-O-isopropylidene-hexofuranurono-6,3-lactones (VI and VII) gave 5-acylamino-5-deoxy-D-glucofuranurono-6,3-lactone (VIII) and 5-acylamino-5-deoxy-L-idofuranurono-6,3-lactone (IX), respectively. Catalytic oxidation of IXa and VIIIa using Adams' catalyst gave 5-acetamido-5-deoxysaccharo-6,3-lactones (XI and XII), and gave 5-acetamido-4,5-dideoxy-L-threo-hex-4-enaro-6,3-lactone (XIVa) in the presence of sodium hydrogen carbonate. Some derivatives of XIVa were prepared.
- 公益社団法人日本薬学会の論文
- 1974-10-25
著者
-
越智 清成
Research Laboratories, Chugai Pharmaceutical Co., Ltd.
-
奥井 清
Research Laboratories, Chugai Pharmaceutical Co., Ltd.
-
越智 清成
Exploratory Research Laboratories, Chugai Pharmaceutical Co., Ltd.,
-
越智 清成
Exploratory Research Laboratories Chugai Pharmaceutical Co. Ltd.
-
奥井 清
Research Laboratories Chugai Pharmaceutical Co. Ltd.
関連論文
- The Reactions of (-)-(R)-2-Aminomethylpyrrolidine(1,1-cyclobutanedicarboxylato)platinum(II), Carboplatin and Cisplatin with Guanosine : Kinetic Comparison of the Reactivities
- Reaction of (R)-(-)-2-Aminomethylpyrrolidine(1,1-cyclobutanedicarboxylato)platinum(II) with Guanosine
- Crystalline Salts of Sucrose Octasulfate
- 1-B-9 1α-Hydroxyvitamin D_3の25-水酸化反応とその調節(日本ビタミン学会 : 第28回大会研究発表要旨)
- 5.肝における 1α-Hydroxyvitamin D_3の 1α, 25-Dihydroxyvitamin D_3への代謝(脂溶性ビタミン総合研究委員会 : 第156回会議研究発表要旨)
- Syntheses and Biological Activities of N^1-(2-Formylethyl)-5-fluorouracil and Related Compounds
- The Convenient Synthesis of 25-Hydroxycholesterol
- Synthesis of 1α, 24 (R)- and 1α, 24 (S)-Dihydroxycholesterol from Cholic Acid Derivatives
- SYNTHETIC STUDIES OF VITAMIN D ANALOGUES. VII. : SYNTHESIS OF 20-OXA-21-NORVITAMIN D_3 ANALOGUES
- A Facile Synthetic Method for Pyrimidine Acyclonucleoside Derivatives
- Synthetic Studies of Vitamin D Analogues. XIV. Synthesis and Calcium Regulating Activity of Vitamin D_3 Analogues Bearing a Hydroxyalkoxy Group at the 2β-Position
- Asymmetric Reduction of 2-Aminobenzophenone Using Yeast, Rhodosporidium toruloides
- Studies on Amino Sugars. I. Synthesis of 5-Amino-5-deoxyuronic Acid and 5-Amino-5-deoxysaccharic Acid Derivatives from D-Glucuronolactone
- Derivees des Pyrimidines. II. Synthese des Alcocy-2-Pyrimidyl-4)-N^1-Sulfanilamides
- Pyrimidine Derivatives. I. Synthesis of a New Series of Sulfanilamides having Dialkylamino Groups in the Pyrimidine Nucleus
- Pyridopyridazines. III. Pyrido [3,4-d] pyridazines. I.