Stereoselective Total Synthesis of 1,4-Dideoxy-1,4-imino-L-ribitol by an Intramolecular Ring Opening of Epoxide with a Tethered Amide-Reference-Cited by-同舟云学术

Stereoselective Total Synthesis of 1,4-Dideoxy-1,4-imino-L-ribitol by an Intramolecular Ring Opening of Epoxide with a Tethered Amide

Published:2018-08 Issue:8 Volume:13 Page:1934578X1801300
ISSN:1934-578X
Container-title:Natural Product Communications
language:en
Short-container-title:Natural Product Communications

Author:

Dhudmal Chaya N¹,Biradar Dhanraj O¹,Satyanarayana Maddipatla V.¹,Reddy Basi V Subba¹

Affiliation:

1. Centre for Semiochemicals, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500 007, India

Abstract

Stereoselective total synthesis of 1,4-dideoxy-1,4-imino-L-ribitol has been accomplished from D-glucose. The key step involved in this synthesis is the regioselective ring-opening of the epoxide with a tethered amido group to give the N-tosyl-3,6-dideoxy-3,6-imino-1,2- O-isopropylidene-α-D-glucofuranose.

Publisher

SAGE Publications

Subject

Complementary and alternative medicine,Plant Science,Drug Discovery,Pharmacology,General Medicine

Link

http://journals.sagepub.com/doi/pdf/10.1177/1934578X1801300821

Reference13 articles.

1. Asymmetric Dihydroxylation of d-Glucose Derived α,β-Unsaturated Ester: Synthesis of Azepane and Nojirimycin Analogues

2. Synthesis of azasugars as potent inhibitors of glycosidases

3. Looking glass inhibitors: both enantiomeric N-benzyl derivatives of 1,4-dideoxy-1,4-imino-d-lyxitol [a potent competitive inhibitor of α-d-galactosidase] and of 1,4-dideoxy-1,4-imino-l-lyxitol [a weak competitive inhibitor of α-d-galactosidase] inhibit naringinase, an α-l-rhamnosidase competitively

4. Synthesis from D-lyxonolactone of 1,4-Dideoxy-1,4-imino-L-arabinitol, a glucosidase inhibitor with in vitro anti-viral activity

5. Inhibition of HIV replication by amino-sugar derivatives

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