Regioselective Synthesis of Inositol Phosphate Diesters via a Cyclic Phosphate Triester Approach

Carsten Schultz; Thomas Metschies; Benjamin Gerlach; Christoph Stadler; Bernd Jastorff

doi:10.1055/s-1990-21022

Regioselective Synthesis of Inositol Phosphate Diesters via a Cyclic Phosphate Triester Approach

Carsten Schultz, Thomas Metschies, Benjamin Gerlach, Christoph Stadler, Bernd Jastorff

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

6 Scopus citations

Abstract

Phosphate-substituted analogues of myo-inositol 1-phosphate and 2-phosphate were synthesized by a novel method via a five-membered cyclic phosphate triester intermediate, which was cleaved regioselectively by various alcohols. Low temperatures and bulky alcohols gave higher selectivity for myo-inositol 1-phosphate alkyl esters. Addition of sodium sulfite to the reaction mixture yielded predominantly the 2-phosphate diester.

Original language	English (US)
Pages (from-to)	163-165
Number of pages	3
Journal	Synlett
Volume	1990
Issue number	3
DOIs	https://doi.org/10.1055/s-1990-21022
State	Published - Mar 1990
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "Regioselective Synthesis of Inositol Phosphate Diesters via a Cyclic Phosphate Triester Approach",

abstract = "Phosphate-substituted analogues of myo-inositol 1-phosphate and 2-phosphate were synthesized by a novel method via a five-membered cyclic phosphate triester intermediate, which was cleaved regioselectively by various alcohols. Low temperatures and bulky alcohols gave higher selectivity for myo-inositol 1-phosphate alkyl esters. Addition of sodium sulfite to the reaction mixture yielded predominantly the 2-phosphate diester.",

author = "Carsten Schultz and Thomas Metschies and Benjamin Gerlach and Christoph Stadler and Bernd Jastorff",

year = "1990",

month = mar,

doi = "10.1055/s-1990-21022",

language = "English (US)",

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T1 - Regioselective Synthesis of Inositol Phosphate Diesters via a Cyclic Phosphate Triester Approach

AU - Schultz, Carsten

AU - Metschies, Thomas

AU - Gerlach, Benjamin

AU - Stadler, Christoph

AU - Jastorff, Bernd

PY - 1990/3

Y1 - 1990/3

N2 - Phosphate-substituted analogues of myo-inositol 1-phosphate and 2-phosphate were synthesized by a novel method via a five-membered cyclic phosphate triester intermediate, which was cleaved regioselectively by various alcohols. Low temperatures and bulky alcohols gave higher selectivity for myo-inositol 1-phosphate alkyl esters. Addition of sodium sulfite to the reaction mixture yielded predominantly the 2-phosphate diester.

AB - Phosphate-substituted analogues of myo-inositol 1-phosphate and 2-phosphate were synthesized by a novel method via a five-membered cyclic phosphate triester intermediate, which was cleaved regioselectively by various alcohols. Low temperatures and bulky alcohols gave higher selectivity for myo-inositol 1-phosphate alkyl esters. Addition of sodium sulfite to the reaction mixture yielded predominantly the 2-phosphate diester.

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U2 - 10.1055/s-1990-21022

DO - 10.1055/s-1990-21022

M3 - Article

AN - SCOPUS:0042560562

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JO - Synlett

JF - Synlett

IS - 3

ER -

Regioselective Synthesis of Inositol Phosphate Diesters via a Cyclic Phosphate Triester Approach

Abstract

ASJC Scopus subject areas

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