Reduction studies of antifungal echinocandin lipopeptides. One step conversion of echinocandin B to echinocandin C.

James M. Balkovec; Regina M. Black

doi:10.1016/S0040-4039(00)61304-7

Reduction studies of antifungal echinocandin lipopeptides. One step conversion of echinocandin B to echinocandin C.

James M. Balkovec
, Regina M. Black

Center for Discovery and Innovation

Merck

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

24 Scopus citations

Abstract

Sodium cyanoborohydride in trifluoroacetic acid selectively reduced the C5-orn and C4-htyr carbinols to methylene groups in echinocandin lipopeptides. The selective reduction of either hydroxyl is also described. The first conversion of echinocandin B to echinocandin C was accomplished.

Original language	English
Pages (from-to)	4529-4532
Number of pages	4
Journal	Tetrahedron Letters
Volume	33
Issue number	32
DOIs	https://doi.org/10.1016/S0040-4039(00)61304-7
State	Published - 4 Aug 1992

Keywords

1,3-β-Glucan Synthesis Inhibitor
Antifungal
Selective Reduction
Sodium Cyanoborohydride-TFA
Sodium Triacetoxyborohydride-TFA

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10.1016/S0040-4039(00)61304-7

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title = "Reduction studies of antifungal echinocandin lipopeptides. One step conversion of echinocandin B to echinocandin C.",

abstract = "Sodium cyanoborohydride in trifluoroacetic acid selectively reduced the C5-orn and C4-htyr carbinols to methylene groups in echinocandin lipopeptides. The selective reduction of either hydroxyl is also described. The first conversion of echinocandin B to echinocandin C was accomplished.",

keywords = "1,3-β-Glucan Synthesis Inhibitor, Antifungal, Selective Reduction, Sodium Cyanoborohydride-TFA, Sodium Triacetoxyborohydride-TFA",

author = "Balkovec, \{James M.\} and Black, \{Regina M.\}",

year = "1992",

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doi = "10.1016/S0040-4039(00)61304-7",

language = "English",

volume = "33",

pages = "4529--4532",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Reduction studies of antifungal echinocandin lipopeptides. One step conversion of echinocandin B to echinocandin C.

AU - Balkovec, James M.

AU - Black, Regina M.

PY - 1992/8/4

Y1 - 1992/8/4

N2 - Sodium cyanoborohydride in trifluoroacetic acid selectively reduced the C5-orn and C4-htyr carbinols to methylene groups in echinocandin lipopeptides. The selective reduction of either hydroxyl is also described. The first conversion of echinocandin B to echinocandin C was accomplished.

AB - Sodium cyanoborohydride in trifluoroacetic acid selectively reduced the C5-orn and C4-htyr carbinols to methylene groups in echinocandin lipopeptides. The selective reduction of either hydroxyl is also described. The first conversion of echinocandin B to echinocandin C was accomplished.

KW - 1,3-β-Glucan Synthesis Inhibitor

KW - Antifungal

KW - Selective Reduction

KW - Sodium Cyanoborohydride-TFA

KW - Sodium Triacetoxyborohydride-TFA

UR - https://www.scopus.com/pages/publications/0026766420

U2 - 10.1016/S0040-4039(00)61304-7

DO - 10.1016/S0040-4039(00)61304-7

M3 - Article

AN - SCOPUS:0026766420

SN - 0040-4039

VL - 33

SP - 4529

EP - 4532

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 32

ER -

Reduction studies of antifungal echinocandin lipopeptides. One step conversion of echinocandin B to echinocandin C.

Abstract

Keywords

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