Synthesis of the (α,α-difluoroalkyl)phosphonate analogue of phosphoserine

David B. Berkowitz; Quanrong Shen; Jun Ho Maeng

doi:10.1016/S0040-4039(00)78242-6

Synthesis of the (α,α-difluoroalkyl)phosphonate analogue of phosphoserine

David B. Berkowitz, Quanrong Shen, Jun Ho Maeng

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Abstract

The synthesis of the (α,α-difluoroalkyl)phosphonate analogue of L-phosphoserine, 5, in a form appropriate for solid phase peptide synthesis, is reported. Two independent routes are described, starting from L-serine or (R)-isopropylideneglycerol. In each case, PCF₂C bond formation is achieved by triflate displacement with diethyl lithiodifluoromethylphosphonate.

Original language	English (US)
Pages (from-to)	6445-6448
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	35
DOIs	https://doi.org/10.1016/S0040-4039(00)78242-6
State	Published - Aug 29 1994

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Synthesis of the (α,α-difluoroalkyl)phosphonate analogue of phosphoserine",

abstract = "The synthesis of the (α,α-difluoroalkyl)phosphonate analogue of L-phosphoserine, 5, in a form appropriate for solid phase peptide synthesis, is reported. Two independent routes are described, starting from L-serine or (R)-isopropylideneglycerol. In each case, PCF2C bond formation is achieved by triflate displacement with diethyl lithiodifluoromethylphosphonate.",

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AU - Berkowitz, David B.

AU - Shen, Quanrong

AU - Maeng, Jun Ho

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Y1 - 1994/8/29

N2 - The synthesis of the (α,α-difluoroalkyl)phosphonate analogue of L-phosphoserine, 5, in a form appropriate for solid phase peptide synthesis, is reported. Two independent routes are described, starting from L-serine or (R)-isopropylideneglycerol. In each case, PCF2C bond formation is achieved by triflate displacement with diethyl lithiodifluoromethylphosphonate.

AB - The synthesis of the (α,α-difluoroalkyl)phosphonate analogue of L-phosphoserine, 5, in a form appropriate for solid phase peptide synthesis, is reported. Two independent routes are described, starting from L-serine or (R)-isopropylideneglycerol. In each case, PCF2C bond formation is achieved by triflate displacement with diethyl lithiodifluoromethylphosphonate.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Synthesis of the (α,α-difluoroalkyl)phosphonate analogue of phosphoserine

Abstract

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