Diversity oriented synthesis of pyran based polyfunctional stereogenic macrocyles and their conformational studies

Arya Ajay; Shrikant Sharma; Munna Prasad Gupt; Vikas Bajpai; Hamidullah; Brijesh Kumar; Mahabir Prasad Kaushik; Rituraj Konwar; Ravi Sankar Ampapathi; Rama Pati Tripathi

doi:10.1021/ol3022275

Diversity oriented synthesis of pyran based polyfunctional stereogenic macrocyles and their conformational studies

Org Lett. 2012 Sep 7;14(17):4306-9. doi: 10.1021/ol3022275. Epub 2012 Aug 29.

Authors

Arya Ajay¹, Shrikant Sharma, Munna Prasad Gupt, Vikas Bajpai, Hamidullah, Brijesh Kumar, Mahabir Prasad Kaushik, Rituraj Konwar, Ravi Sankar Ampapathi, Rama Pati Tripathi

Affiliation

¹ Medicinal and Process Chemistry Division, Sophisticated Analytical Instrumentation Facility, Endocrinology Division, CSIR-Central Drug Research Institute, Lucknow-226001, U.P., India.

PMID: 22931313
DOI: 10.1021/ol3022275

Abstract

A new approach to synthesize a homologous series of 14-, 15-, and 16-membered drug-like, macrocyclic glycoconjugates involving TBAHS promoted azide-propenone intramolecular cycloaddition in designed C-glycopyranosyl butenones from a simple sugar d-glucose and d-mannose is reported.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Glucose / chemistry
Glycoconjugates / chemical synthesis*
Glycoconjugates / chemistry
Macrocyclic Compounds / chemical synthesis*
Macrocyclic Compounds / chemistry
Mannose / chemistry
Molecular Conformation
Molecular Structure
Pyrans / chemical synthesis*
Pyrans / chemistry
Stereoisomerism

Substances

Glycoconjugates
Macrocyclic Compounds
Pyrans
Glucose
Mannose