Stereoselective synthesis of β-C-allyl- and β-C-propargyl-D- arabinofuranosides

C. V. Ramana; Sachin B. Narute; Rajesh G. Gonnade; Rahul S. Patil

doi:10.1055/s-2008-1067016

Stereoselective synthesis of β-C-allyl- and β-C-propargyl-D- arabinofuranosides

C. V. Ramana, Sachin B. Narute, Rajesh G. Gonnade, Rahul S. Patil

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

6 Scopus citations

Abstract

The stereoselective synthesis of β-configured C-allyl-and C-propargyl-D-arabinofuranosides (4,7-anhydro-l,2,3-deoxy-D-gluco-oct-1-enitols and -oct-1-ynitols) was addressed by employing allylation/propargylation of a dialdofuranose under aqueous Barbier reaction conditions and acid-catalyzed furan ring transposition of 5-O-mesyl-manno-oct-7-eno- or 5-O-mesyl-manno-oct-7- ynofuranoside derivatives.

Original language	English
Pages (from-to)	1783-1787
Number of pages	5
Journal	Synthesis
Issue number	11
DOIs	https://doi.org/10.1055/s-2008-1067016
State	Published - 2 Jun 2008
Externally published	Yes

Keywords

Allylation
Barbier reaction
C-glycoside
D-mannose
Propargylation
Ring transposition

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1055/s-2008-1067016

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title = "Stereoselective synthesis of β-C-allyl- and β-C-propargyl-D- arabinofuranosides",

abstract = "The stereoselective synthesis of β-configured C-allyl-and C-propargyl-D-arabinofuranosides (4,7-anhydro-l,2,3-deoxy-D-gluco-oct-1-enitols and -oct-1-ynitols) was addressed by employing allylation/propargylation of a dialdofuranose under aqueous Barbier reaction conditions and acid-catalyzed furan ring transposition of 5-O-mesyl-manno-oct-7-eno- or 5-O-mesyl-manno-oct-7- ynofuranoside derivatives.",

keywords = "Allylation, Barbier reaction, C-glycoside, D-mannose, Propargylation, Ring transposition",

author = "Ramana, \{C. V.\} and Narute, \{Sachin B.\} and Gonnade, \{Rajesh G.\} and Patil, \{Rahul S.\}",

year = "2008",

month = jun,

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doi = "10.1055/s-2008-1067016",

language = "English",

pages = "1783--1787",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "11",

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TY - JOUR

T1 - Stereoselective synthesis of β-C-allyl- and β-C-propargyl-D- arabinofuranosides

AU - Ramana, C. V.

AU - Narute, Sachin B.

AU - Gonnade, Rajesh G.

AU - Patil, Rahul S.

PY - 2008/6/2

Y1 - 2008/6/2

N2 - The stereoselective synthesis of β-configured C-allyl-and C-propargyl-D-arabinofuranosides (4,7-anhydro-l,2,3-deoxy-D-gluco-oct-1-enitols and -oct-1-ynitols) was addressed by employing allylation/propargylation of a dialdofuranose under aqueous Barbier reaction conditions and acid-catalyzed furan ring transposition of 5-O-mesyl-manno-oct-7-eno- or 5-O-mesyl-manno-oct-7- ynofuranoside derivatives.

AB - The stereoselective synthesis of β-configured C-allyl-and C-propargyl-D-arabinofuranosides (4,7-anhydro-l,2,3-deoxy-D-gluco-oct-1-enitols and -oct-1-ynitols) was addressed by employing allylation/propargylation of a dialdofuranose under aqueous Barbier reaction conditions and acid-catalyzed furan ring transposition of 5-O-mesyl-manno-oct-7-eno- or 5-O-mesyl-manno-oct-7- ynofuranoside derivatives.

KW - Allylation

KW - Barbier reaction

KW - C-glycoside

KW - D-mannose

KW - Propargylation

KW - Ring transposition

UR - https://www.scopus.com/pages/publications/45249103957

U2 - 10.1055/s-2008-1067016

DO - 10.1055/s-2008-1067016

M3 - Article

AN - SCOPUS:45249103957

SN - 0039-7881

SP - 1783

EP - 1787

JO - Synthesis

JF - Synthesis

IS - 11

ER -

Stereoselective synthesis of β-C-allyl- and β-C-propargyl-D- arabinofuranosides

Abstract

Keywords

ASJC Scopus subject areas

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