Synthesis of the Carbohydrate Moiety of Bleomycin

Vince Pozsgay; Tadaaki Ohgi; Sidney M. Hecht

doi:10.1021/jo00331a048

Synthesis of the Carbohydrate Moiety of Bleomycin

Vince Pozsgay, Tadaaki Ohgi, Sidney M. Hecht

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12 Scopus citations

Abstract

The synthesis of the disaccharide 2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranose has been achieved in good yield via the silver triflate promoted coupling of 2,4,6-tri-O-acetyl-3-O-(N-acetylcarbamoyl)-α-D-mannopyranosyl bromide (7) with both benzyl 3,4,6-tri-O-benzyl-β-L-gulopyranoside (5) and 3,4-di-O-benzyl-1,6-anhydro-β-L-gulopyranose (12).

Original language	English (US)
Pages (from-to)	3761-3763
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	46
Issue number	18
DOIs	https://doi.org/10.1021/jo00331a048
State	Published - Aug 1981
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "Synthesis of the Carbohydrate Moiety of Bleomycin",

abstract = "The synthesis of the disaccharide 2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranose has been achieved in good yield via the silver triflate promoted coupling of 2,4,6-tri-O-acetyl-3-O-(N-acetylcarbamoyl)-α-D-mannopyranosyl bromide (7) with both benzyl 3,4,6-tri-O-benzyl-β-L-gulopyranoside (5) and 3,4-di-O-benzyl-1,6-anhydro-β-L-gulopyranose (12).",

author = "Vince Pozsgay and Tadaaki Ohgi and Hecht, {Sidney M.}",

year = "1981",

month = aug,

doi = "10.1021/jo00331a048",

language = "English (US)",

volume = "46",

pages = "3761--3763",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "18",

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T1 - Synthesis of the Carbohydrate Moiety of Bleomycin

AU - Pozsgay, Vince

AU - Ohgi, Tadaaki

AU - Hecht, Sidney M.

PY - 1981/8

Y1 - 1981/8

N2 - The synthesis of the disaccharide 2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranose has been achieved in good yield via the silver triflate promoted coupling of 2,4,6-tri-O-acetyl-3-O-(N-acetylcarbamoyl)-α-D-mannopyranosyl bromide (7) with both benzyl 3,4,6-tri-O-benzyl-β-L-gulopyranoside (5) and 3,4-di-O-benzyl-1,6-anhydro-β-L-gulopyranose (12).

AB - The synthesis of the disaccharide 2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranose has been achieved in good yield via the silver triflate promoted coupling of 2,4,6-tri-O-acetyl-3-O-(N-acetylcarbamoyl)-α-D-mannopyranosyl bromide (7) with both benzyl 3,4,6-tri-O-benzyl-β-L-gulopyranoside (5) and 3,4-di-O-benzyl-1,6-anhydro-β-L-gulopyranose (12).

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DO - 10.1021/jo00331a048

M3 - Article

AN - SCOPUS:0019801636

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SP - 3761

EP - 3763

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 18

ER -

Synthesis of the Carbohydrate Moiety of Bleomycin

Abstract

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