Alternative syntheses of l-(-)-oleandrose from l-rhamnose1 preparation of glycals

Martin Bredenkamp; Cedric W. Holzapfel; Francois Toerien

doi:10.1080/00397919208021642

Alternative syntheses of l-(-)-oleandrose from l-rhamnose¹ preparation of glycals

Martin Bredenkamp, Cedric W. Holzapfel, Francois Toerien

Chemical Sciences

University of Johannesburg

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

32 Citations (Scopus)

Abstract

L-Rhamnal (2) is prepared from L-rhamnose (3) by use of an improved generalized Fischer-Zach reaction. L-Rhamnal (2) is then converted to L-(-)-oIeandrose (1) by stannylene mediated selective methylation and effective hydration. Benzyl α-L-oleandrose (12) is prepared by selective methylation and deoxygenation of L-rhamnose (3).

Original language	English
Pages (from-to)	2459-2477
Number of pages	19
Journal	Synthetic Communications
Volume	22
Issue number	17
DOIs	https://doi.org/10.1080/00397919208021642
Publication status	Published - 1 Sept 1992

ASJC Scopus subject areas

Organic Chemistry

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10.1080/00397919208021642

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title = "Alternative syntheses of l-(-)-oleandrose from l-rhamnose1 preparation of glycals",

abstract = "L-Rhamnal (2) is prepared from L-rhamnose (3) by use of an improved generalized Fischer-Zach reaction. L-Rhamnal (2) is then converted to L-(-)-oIeandrose (1) by stannylene mediated selective methylation and effective hydration. Benzyl α-L-oleandrose (12) is prepared by selective methylation and deoxygenation of L-rhamnose (3).",

author = "Martin Bredenkamp and Holzapfel, \{Cedric W.\} and Francois Toerien",

year = "1992",

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AU - Bredenkamp, Martin

AU - Holzapfel, Cedric W.

AU - Toerien, Francois

PY - 1992/9/1

Y1 - 1992/9/1

N2 - L-Rhamnal (2) is prepared from L-rhamnose (3) by use of an improved generalized Fischer-Zach reaction. L-Rhamnal (2) is then converted to L-(-)-oIeandrose (1) by stannylene mediated selective methylation and effective hydration. Benzyl α-L-oleandrose (12) is prepared by selective methylation and deoxygenation of L-rhamnose (3).

AB - L-Rhamnal (2) is prepared from L-rhamnose (3) by use of an improved generalized Fischer-Zach reaction. L-Rhamnal (2) is then converted to L-(-)-oIeandrose (1) by stannylene mediated selective methylation and effective hydration. Benzyl α-L-oleandrose (12) is prepared by selective methylation and deoxygenation of L-rhamnose (3).

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DO - 10.1080/00397919208021642

M3 - Article

AN - SCOPUS:0026739215

SN - 0039-7911

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JO - Synthetic Communications

JF - Synthetic Communications

IS - 17

ER -

Alternative syntheses of l-(-)-oleandrose from l-rhamnose¹ preparation of glycals

Abstract

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