Syntheses of ethyl 3-deoxy-3,3-difluoro-d-arabino-heptulosonate and analogues

Yuan Li; Michael G.B. Drew; Elizabeth V  Welchman; RAJEEV SHRIVASTAVA; Shende Jiang; Roy  Valentine; Gurdial  Singh

doi:10.1016/j.tet.2004.06.048

Syntheses of ethyl 3-deoxy-3,3-difluoro-d-arabino-heptulosonate and analogues

Yuan Li
, Michael G.B. Drew
, Elizabeth V Welchman
, RAJEEV SHRIVASTAVA
, Shende Jiang
, Roy Valentine
, Gurdial Singh^*

^*Corresponding author for this work

Biology

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

19 Citations (Scopus)

Abstract

The difluorinated analogues of 3-deoxy-d-arabino-heptulosonic acid (DAH) 12, 24 and its enantiomer have been synthesised from d- and l-erythrose via a Reformatsky reaction which gave a mixture of diastereoiosmers in favour of the anti isomer.

The difluorinated analogues of 3-deoxy-d-arabino-heptulosonic acid (DAH) 12, 20 and its enantiomer have been synthesised from d- and l-erythrose via a Reformatsky reaction which gave a mixture of diastereoiosmers in favour of the anti isomer.

Original language	English
Pages (from-to)	6523-6531
Number of pages	9
Journal	Tetrahedron
Volume	60
Issue number	31
DOIs	https://doi.org/10.1016/j.tet.2004.06.048
Publication status	Published - 26 Jul 2004

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title = "Syntheses of ethyl 3-deoxy-3,3-difluoro-d-arabino-heptulosonate and analogues",

abstract = "The difluorinated analogues of 3-deoxy-d-arabino-heptulosonic acid (DAH) 12, 24 and its enantiomer have been synthesised from d- and l-erythrose via a Reformatsky reaction which gave a mixture of diastereoiosmers in favour of the anti isomer. The difluorinated analogues of 3-deoxy-d-arabino-heptulosonic acid (DAH) 12, 20 and its enantiomer have been synthesised from d- and l-erythrose via a Reformatsky reaction which gave a mixture of diastereoiosmers in favour of the anti isomer.",

author = "Yuan Li and Drew, \{Michael G.B.\} and Welchman, \{Elizabeth V\} and RAJEEV SHRIVASTAVA and Shende Jiang and Roy Valentine and Gurdial Singh",

year = "2004",

month = jul,

day = "26",

doi = "10.1016/j.tet.2004.06.048",

language = "English",

volume = "60",

pages = "6523--6531",

journal = "Tetrahedron",

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TY - JOUR

T1 - Syntheses of ethyl 3-deoxy-3,3-difluoro-d-arabino-heptulosonate and analogues

AU - Li, Yuan

AU - Drew, Michael G.B.

AU - Welchman, Elizabeth V

AU - SHRIVASTAVA, RAJEEV

AU - Jiang, Shende

AU - Valentine, Roy

AU - Singh, Gurdial

PY - 2004/7/26

Y1 - 2004/7/26

N2 - The difluorinated analogues of 3-deoxy-d-arabino-heptulosonic acid (DAH) 12, 24 and its enantiomer have been synthesised from d- and l-erythrose via a Reformatsky reaction which gave a mixture of diastereoiosmers in favour of the anti isomer. The difluorinated analogues of 3-deoxy-d-arabino-heptulosonic acid (DAH) 12, 20 and its enantiomer have been synthesised from d- and l-erythrose via a Reformatsky reaction which gave a mixture of diastereoiosmers in favour of the anti isomer.

AB - The difluorinated analogues of 3-deoxy-d-arabino-heptulosonic acid (DAH) 12, 24 and its enantiomer have been synthesised from d- and l-erythrose via a Reformatsky reaction which gave a mixture of diastereoiosmers in favour of the anti isomer. The difluorinated analogues of 3-deoxy-d-arabino-heptulosonic acid (DAH) 12, 20 and its enantiomer have been synthesised from d- and l-erythrose via a Reformatsky reaction which gave a mixture of diastereoiosmers in favour of the anti isomer.

U2 - 10.1016/j.tet.2004.06.048

DO - 10.1016/j.tet.2004.06.048

M3 - Article (journal)

SN - 0040-4020

VL - 60

SP - 6523

EP - 6531

JO - Tetrahedron

JF - Tetrahedron

IS - 31

ER -

Syntheses of ethyl 3-deoxy-3,3-difluoro-d-arabino-heptulosonate and analogues

Abstract

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