Glycosyl Nitrates in Synthesis: Streamlined access to Glucopyranose Building Blocks Differentiated at C-2

Tinghua Wang; Swati S. Nigudkar; Jagodige P. Yasomanee; Nigam P. Rath; Keith J. Stine; Alexei V. Demchenko

doi:10.1039/C8OB00477C

Glycosyl Nitrates in Synthesis: Streamlined access to Glucopyranose Building Blocks Differentiated at C-2

Tinghua Wang, Swati S. Nigudkar, Jagodige P. Yasomanee, Nigam P. Rath, Keith J. Stine, Alexei V. Demchenko

University of Missouri-St. Louis

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

Abstract

In an attempt to refine a CAN-mediated synthesis of 1,3,4,6-tetra-O-acetyl-α-D-glucopyranose (2-OH glucose) we unexpectedly discovered that this reaction proceeds via the intermediacy of glycosyl nitrates. Improved mechanistic understanding of this reaction led to the development of a more versatile synthesis of 2-OH glucose from a variety of precursors. Also demonstrated is the conversion of 2-OH glucose into a variety of building blocks differentially protected at C-2, a position that is generally hard to protect regioselectively in the glucopyranose series.

Original language	American English
Journal	Organic and Biomolecular Chemistry
Volume	16
DOIs	https://doi.org/10.1039/C8OB00477C
State	Published - Jan 1 2018

Disciplines

Organic Chemistry
Biochemistry, Biophysics, and Structural Biology
Biochemistry

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10.1039/C8OB00477CLicense: Unspecified

Cite this

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abstract = " In an attempt to refine a CAN-mediated synthesis of 1,3,4,6-tetra-O-acetyl-α-D-glucopyranose (2-OH glucose) we unexpectedly discovered that this reaction proceeds via the intermediacy of glycosyl nitrates. Improved mechanistic understanding of this reaction led to the development of a more versatile synthesis of 2-OH glucose from a variety of precursors. Also demonstrated is the conversion of 2-OH glucose into a variety of building blocks differentially protected at C-2, a position that is generally hard to protect regioselectively in the glucopyranose series.",

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AU - Wang, Tinghua

AU - Nigudkar, Swati S.

AU - Yasomanee, Jagodige P.

AU - Rath, Nigam P.

AU - Stine, Keith J.

AU - Demchenko, Alexei V.

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PY - 2018/1/1

Y1 - 2018/1/1

N2 - In an attempt to refine a CAN-mediated synthesis of 1,3,4,6-tetra-O-acetyl-α-D-glucopyranose (2-OH glucose) we unexpectedly discovered that this reaction proceeds via the intermediacy of glycosyl nitrates. Improved mechanistic understanding of this reaction led to the development of a more versatile synthesis of 2-OH glucose from a variety of precursors. Also demonstrated is the conversion of 2-OH glucose into a variety of building blocks differentially protected at C-2, a position that is generally hard to protect regioselectively in the glucopyranose series.

AB - In an attempt to refine a CAN-mediated synthesis of 1,3,4,6-tetra-O-acetyl-α-D-glucopyranose (2-OH glucose) we unexpectedly discovered that this reaction proceeds via the intermediacy of glycosyl nitrates. Improved mechanistic understanding of this reaction led to the development of a more versatile synthesis of 2-OH glucose from a variety of precursors. Also demonstrated is the conversion of 2-OH glucose into a variety of building blocks differentially protected at C-2, a position that is generally hard to protect regioselectively in the glucopyranose series.

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UR - https://doi.org/10.1039/C8OB00477C

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JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

ER -

Glycosyl Nitrates in Synthesis: Streamlined access to Glucopyranose Building Blocks Differentiated at C-2

Abstract

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