Synthesis of C-disaccharides through a one-pot alkynol cycloisomerization- reductive deoxygenation

Sachin B. Narute; Jeetendra Kumar Rout; Chepuri V. Ramana

doi:10.1002/chem.201302252

Synthesis of C-disaccharides through a one-pot alkynol cycloisomerization- reductive deoxygenation

Sachin B. Narute
, Jeetendra Kumar Rout
, Chepuri V. Ramana

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

9 Scopus citations

Abstract

A sweet disposition: Simple protocols for the synthesis of (1→1)- and (1→6)-linked C-disaccharides have been developed (see scheme). A one-pot Au-catalyzed alkynol cycloisomerization followed by BF₃×Et ₂O, Et₃SiH reduction has been established as the key reaction for C-disaccharide synthesis including all possible pyran-pyran, furan-furan, and pyran-furan combinations.

Original language	English
Pages (from-to)	15109-15114
Number of pages	6
Journal	Chemistry - A European Journal
Volume	19
Issue number	45
DOIs	https://doi.org/10.1002/chem.201302252
State	Published - 4 Nov 2013
Externally published	Yes

Keywords

C-disaccharides
carbohydrates
epoxide-alkyne coupling
gold catalysis
reductive deoxygenation×

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201302252

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title = "Synthesis of C-disaccharides through a one-pot alkynol cycloisomerization- reductive deoxygenation",

abstract = "A sweet disposition: Simple protocols for the synthesis of (1→1)- and (1→6)-linked C-disaccharides have been developed (see scheme). A one-pot Au-catalyzed alkynol cycloisomerization followed by BF3×Et 2O, Et3SiH reduction has been established as the key reaction for C-disaccharide synthesis including all possible pyran-pyran, furan-furan, and pyran-furan combinations.",

keywords = "C-disaccharides, carbohydrates, epoxide-alkyne coupling, gold catalysis, reductive deoxygenation×",

author = "Narute, \{Sachin B.\} and Rout, \{Jeetendra Kumar\} and Ramana, \{Chepuri V.\}",

year = "2013",

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doi = "10.1002/chem.201302252",

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AU - Narute, Sachin B.

AU - Rout, Jeetendra Kumar

AU - Ramana, Chepuri V.

PY - 2013/11/4

Y1 - 2013/11/4

N2 - A sweet disposition: Simple protocols for the synthesis of (1→1)- and (1→6)-linked C-disaccharides have been developed (see scheme). A one-pot Au-catalyzed alkynol cycloisomerization followed by BF3×Et 2O, Et3SiH reduction has been established as the key reaction for C-disaccharide synthesis including all possible pyran-pyran, furan-furan, and pyran-furan combinations.

AB - A sweet disposition: Simple protocols for the synthesis of (1→1)- and (1→6)-linked C-disaccharides have been developed (see scheme). A one-pot Au-catalyzed alkynol cycloisomerization followed by BF3×Et 2O, Et3SiH reduction has been established as the key reaction for C-disaccharide synthesis including all possible pyran-pyran, furan-furan, and pyran-furan combinations.

KW - C-disaccharides

KW - carbohydrates

KW - epoxide-alkyne coupling

KW - gold catalysis

KW - reductive deoxygenation×

UR - https://www.scopus.com/pages/publications/84886639317

U2 - 10.1002/chem.201302252

DO - 10.1002/chem.201302252

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JF - Chemistry - A European Journal

IS - 45

ER -

Synthesis of C-disaccharides through a one-pot alkynol cycloisomerization- reductive deoxygenation

Abstract

Keywords

ASJC Scopus subject areas

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