A Stevens rearrangement thwarts glycosylation with liposidomycin diazepanone ribofuranosyl donors

Spencer Knapp; Gregori J. Morriello; George A. Doss

doi:10.1016/S0040-4039(02)01205-4

A Stevens rearrangement thwarts glycosylation with liposidomycin diazepanone ribofuranosyl donors

Spencer Knapp, Gregori J. Morriello, George A. Doss

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

Abstract

Attempted Vorbrüggen and related glycosylations with ribofuranosyl acetates fail in the liposidomycin series when there is a nucleophilic amine six atoms from the anomeric center. Instead, the nitrogen participates, and a stereoselective Stevens rearrangement ensues.

Original language	English (US)
Pages (from-to)	5797-5800
Number of pages	4
Journal	Tetrahedron Letters
Volume	43
Issue number	33
DOIs	https://doi.org/10.1016/S0040-4039(02)01205-4
State	Published - Aug 12 2002

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(02)01205-4

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title = "A Stevens rearrangement thwarts glycosylation with liposidomycin diazepanone ribofuranosyl donors",

abstract = "Attempted Vorbr{\"u}ggen and related glycosylations with ribofuranosyl acetates fail in the liposidomycin series when there is a nucleophilic amine six atoms from the anomeric center. Instead, the nitrogen participates, and a stereoselective Stevens rearrangement ensues.",

author = "Spencer Knapp and Morriello, {Gregori J.} and Doss, {George A.}",

note = "Funding Information: We are grateful to Merck and Co. and SynChem Research, Inc., for financial support.",

year = "2002",

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T1 - A Stevens rearrangement thwarts glycosylation with liposidomycin diazepanone ribofuranosyl donors

AU - Knapp, Spencer

AU - Morriello, Gregori J.

AU - Doss, George A.

N1 - Funding Information: We are grateful to Merck and Co. and SynChem Research, Inc., for financial support.

PY - 2002/8/12

Y1 - 2002/8/12

N2 - Attempted Vorbrüggen and related glycosylations with ribofuranosyl acetates fail in the liposidomycin series when there is a nucleophilic amine six atoms from the anomeric center. Instead, the nitrogen participates, and a stereoselective Stevens rearrangement ensues.

AB - Attempted Vorbrüggen and related glycosylations with ribofuranosyl acetates fail in the liposidomycin series when there is a nucleophilic amine six atoms from the anomeric center. Instead, the nitrogen participates, and a stereoselective Stevens rearrangement ensues.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

A Stevens rearrangement thwarts glycosylation with liposidomycin diazepanone ribofuranosyl donors

Abstract

All Science Journal Classification (ASJC) codes

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