Synthesis of α-glucuronic acid and amide derivatives in the presence of a participating 2-acyl protecting group

Manuela Tosin; Paul V. Murphy

doi:10.1021/ol026629j

Synthesis of α-glucuronic acid and amide derivatives in the presence of a participating 2-acyl protecting group

Manuela Tosin
, Paul V. Murphy

University College Dublin

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

77 Citations (Scopus)

Abstract

(graph presented) Participating acyl groups located at C-2 in glucosyl and related donors generally promote formation of 1,2-trans-glycosides. Reactions of some glucuronic acid donors with TMSN₃/SnCl₄ or ROH/SnCl₄ gave only the 1,2-cis-glycoside. The stereoselectivity is consistent with participation of the C-6 group. The methodology was used for the synthesis of a Kdn2en mimetic with the α-configuration.

Original language	English
Pages (from-to)	3675-3678
Number of pages	4
Journal	Organic Letters
Volume	4
Issue number	21
DOIs	https://doi.org/10.1021/ol026629j
Publication status	Published - 17 Oct 2002
Externally published	Yes

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title = "Synthesis of α-glucuronic acid and amide derivatives in the presence of a participating 2-acyl protecting group",

abstract = "(graph presented) Participating acyl groups located at C-2 in glucosyl and related donors generally promote formation of 1,2-trans-glycosides. Reactions of some glucuronic acid donors with TMSN3/SnCl4 or ROH/SnCl4 gave only the 1,2-cis-glycoside. The stereoselectivity is consistent with participation of the C-6 group. The methodology was used for the synthesis of a Kdn2en mimetic with the α-configuration.",

author = "Manuela Tosin and Murphy, \{Paul V.\}",

year = "2002",

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doi = "10.1021/ol026629j",

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volume = "4",

pages = "3675--3678",

journal = "Organic Letters",

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T1 - Synthesis of α-glucuronic acid and amide derivatives in the presence of a participating 2-acyl protecting group

AU - Tosin, Manuela

AU - Murphy, Paul V.

PY - 2002/10/17

Y1 - 2002/10/17

N2 - (graph presented) Participating acyl groups located at C-2 in glucosyl and related donors generally promote formation of 1,2-trans-glycosides. Reactions of some glucuronic acid donors with TMSN3/SnCl4 or ROH/SnCl4 gave only the 1,2-cis-glycoside. The stereoselectivity is consistent with participation of the C-6 group. The methodology was used for the synthesis of a Kdn2en mimetic with the α-configuration.

AB - (graph presented) Participating acyl groups located at C-2 in glucosyl and related donors generally promote formation of 1,2-trans-glycosides. Reactions of some glucuronic acid donors with TMSN3/SnCl4 or ROH/SnCl4 gave only the 1,2-cis-glycoside. The stereoselectivity is consistent with participation of the C-6 group. The methodology was used for the synthesis of a Kdn2en mimetic with the α-configuration.

UR - https://www.scopus.com/pages/publications/0037126209

U2 - 10.1021/ol026629j

DO - 10.1021/ol026629j

M3 - Article

C2 - 12375916

AN - SCOPUS:0037126209

SN - 1523-7060

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SP - 3675

EP - 3678

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Synthesis of α-glucuronic acid and amide derivatives in the presence of a participating 2-acyl protecting group

Abstract

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