An efficient stereoconvergent synthesis of the 4-ethylamino-2,4-dideoxy-l-threo-pentopyranose component of the calicheamicins and esperamicins

Eugene A. Mash; Sandeep K. Nimkar

doi:10.1016/0040-4039(93)85082-8

An efficient stereoconvergent synthesis of the 4-ethylamino-2,4-dideoxy-l-threo-pentopyranose component of the calicheamicins and esperamicins

Eugene A. Mash, Sandeep K. Nimkar

Chemistry and Biochemistry

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

9 Scopus citations

Abstract

A stereconvergent synthesis of the 4-ethylamino-2,4-dideoxy-L-threo-pentopyranose coonponent of calicheamicins γ₁, γ₁^I, α₂^I, and esperamicin A_1b from methyl 2-deoxy-β-D-ribopyranoside is described. The synthesis requires eight steps in each branch. The overall yield is 54%. This synthesis should be adaptable for syntheses of the corresponding 4-methylamino)-2,4-dideoxy- L-threo- and 4-isopropylamino-2.4- dideoxy-L-threo- pentopyranose components of other calicheamicin and esperamicin antibiotics.

Original language	English (US)
Pages (from-to)	385-388
Number of pages	4
Journal	Tetrahedron Letters
Volume	34
Issue number	3
DOIs	https://doi.org/10.1016/0040-4039(93)85082-8
State	Published - Jan 15 1993

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "An efficient stereoconvergent synthesis of the 4-ethylamino-2,4-dideoxy-l-threo-pentopyranose component of the calicheamicins and esperamicins",

abstract = "A stereconvergent synthesis of the 4-ethylamino-2,4-dideoxy-L-threo-pentopyranose coonponent of calicheamicins γ1, γ1I, α2I, and esperamicin A1b from methyl 2-deoxy-β-D-ribopyranoside is described. The synthesis requires eight steps in each branch. The overall yield is 54%. This synthesis should be adaptable for syntheses of the corresponding 4-methylamino)-2,4-dideoxy- L-threo- and 4-isopropylamino-2.4- dideoxy-L-threo- pentopyranose components of other calicheamicin and esperamicin antibiotics.",

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T1 - An efficient stereoconvergent synthesis of the 4-ethylamino-2,4-dideoxy-l-threo-pentopyranose component of the calicheamicins and esperamicins

AU - Mash, Eugene A.

AU - Nimkar, Sandeep K.

PY - 1993/1/15

Y1 - 1993/1/15

N2 - A stereconvergent synthesis of the 4-ethylamino-2,4-dideoxy-L-threo-pentopyranose coonponent of calicheamicins γ1, γ1I, α2I, and esperamicin A1b from methyl 2-deoxy-β-D-ribopyranoside is described. The synthesis requires eight steps in each branch. The overall yield is 54%. This synthesis should be adaptable for syntheses of the corresponding 4-methylamino)-2,4-dideoxy- L-threo- and 4-isopropylamino-2.4- dideoxy-L-threo- pentopyranose components of other calicheamicin and esperamicin antibiotics.

AB - A stereconvergent synthesis of the 4-ethylamino-2,4-dideoxy-L-threo-pentopyranose coonponent of calicheamicins γ1, γ1I, α2I, and esperamicin A1b from methyl 2-deoxy-β-D-ribopyranoside is described. The synthesis requires eight steps in each branch. The overall yield is 54%. This synthesis should be adaptable for syntheses of the corresponding 4-methylamino)-2,4-dideoxy- L-threo- and 4-isopropylamino-2.4- dideoxy-L-threo- pentopyranose components of other calicheamicin and esperamicin antibiotics.

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An efficient stereoconvergent synthesis of the 4-ethylamino-2,4-dideoxy-l-threo-pentopyranose component of the calicheamicins and esperamicins

Abstract

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