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Literature DB >> 24637047

Toward synthesis of carbasugars (+)-gabosine C, (+)-COTC, (+)-pericosine B, and (+)-pericosine C.

D Chanti Babu¹, Ch Bhujanga Rao², K Venkatesham², J Jon Paul Selvam², Y Venkateswarlu².

Abstract

Asymmetric total synthesis of (+)-gabosine C, (+)-pericosine B, and (+)-pericosine C has been reported from readily available d-(-)-isoascorbic acid and d-ribose involving Grubbs ring closing metathesis, Morita-Baylis-Hillman (MBH) reaction, and Luche reduction.

Entities: Chemical

Keywords: Carbasugars; Luche reduction d-(−)-isoascorbic acid and d-ribose; Morita–Baylis–Hillman (MBH) reaction; Periconia byssoides; Streptomyces

Mesh：

Substances：

Year: 2013 PMID： 24637047 DOI： 10.1016/j.carres.2013.08.008

Source DB: PubMed Journal: Carbohydr Res ISSN： 0008-6215 Impact factor: 2.104

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Cited

5 in total

1. Synthesis of Natural O-Linked Carba-Disaccharides, (+)- and (-)-Pericosine E, and Their Analogues as α-Glucosidase Inhibitors.

Authors: Yoshihide Usami; Koji Mizuki; Rikiya Kawahata; Makio Shibano; Atsuko Sekine; Hiroki Yoneyama; Shinya Harusawa
Journal: Mar Drugs Date: 2017-01-23 Impact factor: 5.118

2. Syntheses and Glycosidase Inhibitory Activities, and in Silico Docking Studies of Pericosine E Analogs Methoxy-Substituted at C6.

Authors: Yoshihide Usami; Megumi Higuchi; Koji Mizuki; Mizuki Yamamoto; Mao Kanki; Chika Nakasone; Yuya Sugimoto; Makio Shibano; Yoshihiro Uesawa; Junko Nagai; Hiroki Yoneyama; Shinya Harusawa
Journal: Mar Drugs Date: 2020-04-20 Impact factor: 5.118

Toward synthesis of carbasugars (+)-gabosine C, (+)-COTC, (+)-pericosine B, and (+)-pericosine C.

1. Synthesis of Natural O-Linked Carba-Disaccharides, (+)- and (-)-Pericosine E, and Their Analogues as α-Glucosidase Inhibitors.

2. Syntheses and Glycosidase Inhibitory Activities, and in Silico Docking Studies of Pericosine E Analogs Methoxy-Substituted at C6.

Review 3. Current Synthetic Approaches to the Synthesis of Carbasugars from Non-Carbohydrate Sources.

4. Gram-scale carbasugar synthesis via intramolecular seleno-Michael/aldol reaction.

5. Synthesis of 6-Halo-Substituted Pericosine A and an Evaluation of Their Antitumor and Antiglycosidase Activities.