Addition of trialkylaluminum reagents to glyconolactones. Synthesis of 1-C-methyl GlcNAc oxazoline and thiazoline

Spencer Knapp; Chunhua Yang; Thomas Haimowitz

doi:10.1016/S0040-4039(02)01506-X

Addition of trialkylaluminum reagents to glyconolactones. Synthesis of 1-C-methyl GlcNAc oxazoline and thiazoline

Spencer Knapp
, Chunhua Yang
, Thomas Haimowitz

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

15 Scopus citations

Abstract

Addition of carbon nucleophiles to 2-acetamido-2-deoxygluconolactones fails for many reagents, but trialkylaluminums add alkyl smoothly. The product of methyl addition to 2-acetamido-2-deoxy-D-gluconolactone has been converted to 1-C-methyl GlcNAc thiazoline, a potential N-acetylhexosaminidase inhibitor, and to an O-protected 1-C-Me GlcNAc oxazoline, a potential 1-C-Me GlcNAc donor.

Original language	English (US)
Pages (from-to)	7101-7104
Number of pages	4
Journal	Tetrahedron Letters
Volume	43
Issue number	39
DOIs	https://doi.org/10.1016/S0040-4039(02)01506-X
State	Published - Sep 23 2002

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(02)01506-X

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title = "Addition of trialkylaluminum reagents to glyconolactones. Synthesis of 1-C-methyl GlcNAc oxazoline and thiazoline",

abstract = "Addition of carbon nucleophiles to 2-acetamido-2-deoxygluconolactones fails for many reagents, but trialkylaluminums add alkyl smoothly. The product of methyl addition to 2-acetamido-2-deoxy-D-gluconolactone has been converted to 1-C-methyl GlcNAc thiazoline, a potential N-acetylhexosaminidase inhibitor, and to an O-protected 1-C-Me GlcNAc oxazoline, a potential 1-C-Me GlcNAc donor.",

author = "Spencer Knapp and Chunhua Yang and Thomas Haimowitz",

note = "Funding Information: We are grateful to Merck \& Co. and Vela Pharmaceuticals Inc. for financial support.",

year = "2002",

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doi = "10.1016/S0040-4039(02)01506-X",

language = "English (US)",

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journal = "Tetrahedron Letters",

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T1 - Addition of trialkylaluminum reagents to glyconolactones. Synthesis of 1-C-methyl GlcNAc oxazoline and thiazoline

AU - Knapp, Spencer

AU - Yang, Chunhua

AU - Haimowitz, Thomas

N1 - Funding Information: We are grateful to Merck & Co. and Vela Pharmaceuticals Inc. for financial support.

PY - 2002/9/23

Y1 - 2002/9/23

N2 - Addition of carbon nucleophiles to 2-acetamido-2-deoxygluconolactones fails for many reagents, but trialkylaluminums add alkyl smoothly. The product of methyl addition to 2-acetamido-2-deoxy-D-gluconolactone has been converted to 1-C-methyl GlcNAc thiazoline, a potential N-acetylhexosaminidase inhibitor, and to an O-protected 1-C-Me GlcNAc oxazoline, a potential 1-C-Me GlcNAc donor.

AB - Addition of carbon nucleophiles to 2-acetamido-2-deoxygluconolactones fails for many reagents, but trialkylaluminums add alkyl smoothly. The product of methyl addition to 2-acetamido-2-deoxy-D-gluconolactone has been converted to 1-C-methyl GlcNAc thiazoline, a potential N-acetylhexosaminidase inhibitor, and to an O-protected 1-C-Me GlcNAc oxazoline, a potential 1-C-Me GlcNAc donor.

UR - https://www.scopus.com/pages/publications/0037163256

UR - https://www.scopus.com/pages/publications/0037163256#tab=citedBy

U2 - 10.1016/S0040-4039(02)01506-X

DO - 10.1016/S0040-4039(02)01506-X

M3 - Article

AN - SCOPUS:0037163256

SN - 0040-4039

VL - 43

SP - 7101

EP - 7104

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 39

ER -

Addition of trialkylaluminum reagents to glyconolactones. Synthesis of 1-C-methyl GlcNAc oxazoline and thiazoline

Abstract

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