Synthesis of methyl 3-deoxy-3-methylaminoarabinopyranoside, a component of some aminoglycoside antibiotics

Stacy W. Remiszewski; Terry R. Stouch; Steven M. Weinreb

doi:10.1016/S0040-4020(01)96517-2

Synthesis of methyl 3-deoxy-3-methylaminoarabinopyranoside, a component of some aminoglycoside antibiotics

Stacy W. Remiszewski
, Terry R. Stouch
, Steven M. Weinreb

Chemistry

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

20 Scopus citations

Abstract

Amino sugar 1 has been synthesized in racemic form as a mixture of anomers from sorbic aldehyde. An intramolecular N-sulfinyl dienophile Diels-Alder strategy was used to stereospecifically generate the chiral centers of pentose 1.

Original language	English (US)
Pages (from-to)	1173-1178
Number of pages	6
Journal	Tetrahedron
Volume	41
Issue number	7
DOIs	https://doi.org/10.1016/S0040-4020(01)96517-2
State	Published - 1985

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(01)96517-2

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title = "Synthesis of methyl 3-deoxy-3-methylaminoarabinopyranoside, a component of some aminoglycoside antibiotics",

abstract = "Amino sugar 1 has been synthesized in racemic form as a mixture of anomers from sorbic aldehyde. An intramolecular N-sulfinyl dienophile Diels-Alder strategy was used to stereospecifically generate the chiral centers of pentose 1.",

author = "Remiszewski, \{Stacy W.\} and Stouch, \{Terry R.\} and Weinreb, \{Steven M.\}",

year = "1985",

doi = "10.1016/S0040-4020(01)96517-2",

language = "English (US)",

volume = "41",

pages = "1173--1178",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "7",

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T1 - Synthesis of methyl 3-deoxy-3-methylaminoarabinopyranoside, a component of some aminoglycoside antibiotics

AU - Remiszewski, Stacy W.

AU - Stouch, Terry R.

AU - Weinreb, Steven M.

PY - 1985

Y1 - 1985

N2 - Amino sugar 1 has been synthesized in racemic form as a mixture of anomers from sorbic aldehyde. An intramolecular N-sulfinyl dienophile Diels-Alder strategy was used to stereospecifically generate the chiral centers of pentose 1.

AB - Amino sugar 1 has been synthesized in racemic form as a mixture of anomers from sorbic aldehyde. An intramolecular N-sulfinyl dienophile Diels-Alder strategy was used to stereospecifically generate the chiral centers of pentose 1.

UR - https://www.scopus.com/pages/publications/0021915788

UR - https://www.scopus.com/pages/publications/0021915788#tab=citedBy

U2 - 10.1016/S0040-4020(01)96517-2

DO - 10.1016/S0040-4020(01)96517-2

M3 - Article

AN - SCOPUS:0021915788

SN - 0040-4020

VL - 41

SP - 1173

EP - 1178

JO - Tetrahedron

JF - Tetrahedron

IS - 7

ER -

Synthesis of methyl 3-deoxy-3-methylaminoarabinopyranoside, a component of some aminoglycoside antibiotics

Abstract

All Science Journal Classification (ASJC) codes

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