A stereoselective route to the sugar-cinnamate unit of Hygromycin A

J. G. Buchanan; D. G. Hill; R. H. Wightman; I. K. Boddy; B. D. Hewitt

doi:10.1016/0040-4020(95)00262-7

A stereoselective route to the sugar-cinnamate unit of Hygromycin A

J. G. Buchanan, D. G. Hill, R. H. Wightman, I. K. Boddy, B. D. Hewitt

School of Engineering & Physical Sciences

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

22 Citations (Scopus)

Abstract

Various aryl 6-deoxy-5-keto-ß-D-arabino-hexofuranosides, including one (42) corresponding to the sugar-cinnamate unit of Hygromycin A (1) have been synthesized by a method in which 6-deoxy-ß-D-glucofuranosides are first prepared, followed by configurational inversion at positions 2 and 3 via 2,3-anhydro-6-deoxy-ß-D-mannofuranosyl intermediates.

Original language	English
Pages (from-to)	6033-6050
Number of pages	18
Journal	Tetrahedron
Volume	51
Issue number	21
DOIs	https://doi.org/10.1016/0040-4020(95)00262-7
Publication status	Published - 1995

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title = "A stereoselective route to the sugar-cinnamate unit of Hygromycin A",

abstract = "Various aryl 6-deoxy-5-keto-{\ss}-D-arabino-hexofuranosides, including one (42) corresponding to the sugar-cinnamate unit of Hygromycin A (1) have been synthesized by a method in which 6-deoxy-{\ss}-D-glucofuranosides are first prepared, followed by configurational inversion at positions 2 and 3 via 2,3-anhydro-6-deoxy-{\ss}-D-mannofuranosyl intermediates.",

author = "Buchanan, {J. G.} and Hill, {D. G.} and Wightman, {R. H.} and Boddy, {I. K.} and Hewitt, {B. D.}",

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T1 - A stereoselective route to the sugar-cinnamate unit of Hygromycin A

AU - Buchanan, J. G.

AU - Hill, D. G.

AU - Wightman, R. H.

AU - Boddy, I. K.

AU - Hewitt, B. D.

PY - 1995

Y1 - 1995

N2 - Various aryl 6-deoxy-5-keto-ß-D-arabino-hexofuranosides, including one (42) corresponding to the sugar-cinnamate unit of Hygromycin A (1) have been synthesized by a method in which 6-deoxy-ß-D-glucofuranosides are first prepared, followed by configurational inversion at positions 2 and 3 via 2,3-anhydro-6-deoxy-ß-D-mannofuranosyl intermediates.

AB - Various aryl 6-deoxy-5-keto-ß-D-arabino-hexofuranosides, including one (42) corresponding to the sugar-cinnamate unit of Hygromycin A (1) have been synthesized by a method in which 6-deoxy-ß-D-glucofuranosides are first prepared, followed by configurational inversion at positions 2 and 3 via 2,3-anhydro-6-deoxy-ß-D-mannofuranosyl intermediates.

U2 - 10.1016/0040-4020(95)00262-7

DO - 10.1016/0040-4020(95)00262-7

M3 - Article

SN - 0040-4020

VL - 51

SP - 6033

EP - 6050

JO - Tetrahedron

JF - Tetrahedron

IS - 21

ER -

A stereoselective route to the sugar-cinnamate unit of Hygromycin A

Abstract

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