Synthesis of all possible regioisomers of scyllo-inositol phosphate

Sung Kee Chung; Yong Uk Kwon; Young Tae Chang; Kwang Hoon Sohn; Jung Han Shin; Kyu Hwan Park; Bong Jin Hong; In Hee Chung

doi:10.1016/S0968-0896(99)00183-2

Synthesis of all possible regioisomers of scyllo-inositol phosphate

Sung Kee Chung
, Yong Uk Kwon
, Young Tae Chang
, Kwang Hoon Sohn
, Jung Han Shin
, Kyu Hwan Park
, Bong Jin Hong
, In Hee Chung

Department of Chemistry & Nanoscience

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

26 Scopus citations

Abstract

scyllo-Inositol is the all equatorial stereoisomer of myo-inositol. All possible 12 regioisomers of scyllo-inositol phosphate were synthesized for the first time via a scyllo-inositol benzoate intermediate, which was derived from a myo-inositol derivative. The stereoinversion of myo-inositol into scyllo-inositol was accomplished by Mitsunobu reaction of the vicinal cis- diol. The requisite intermediates, scyllo-inositol benzoates were obtained by benzoyl migration or random benzoylation, and phosphorylated to give scyllo- IP(n). (C) 1999 Elsevier Science Ltd.

Original language	English
Pages (from-to)	2577-2589
Number of pages	13
Journal	Bioorganic and Medicinal Chemistry
Volume	7
Issue number	11
DOIs	https://doi.org/10.1016/S0968-0896(99)00183-2
State	Published - Nov 1999

Bibliographical note

Funding Information:
This work was supported by the Korea Science and Engineering Foundation/Center for Biofunctional Molecules and the Ministry of Education/Basic Science Research Institute Fund (98-3437).

Keywords

Benzoyl migration
Inositol phosphates
Mitsunobu reaction
scyllo-Inositol

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10.1016/S0968-0896(99)00183-2

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title = "Synthesis of all possible regioisomers of scyllo-inositol phosphate",

abstract = "scyllo-Inositol is the all equatorial stereoisomer of myo-inositol. All possible 12 regioisomers of scyllo-inositol phosphate were synthesized for the first time via a scyllo-inositol benzoate intermediate, which was derived from a myo-inositol derivative. The stereoinversion of myo-inositol into scyllo-inositol was accomplished by Mitsunobu reaction of the vicinal cis- diol. The requisite intermediates, scyllo-inositol benzoates were obtained by benzoyl migration or random benzoylation, and phosphorylated to give scyllo- IP(n). (C) 1999 Elsevier Science Ltd.",

keywords = "Benzoyl migration, Inositol phosphates, Mitsunobu reaction, scyllo-Inositol",

author = "Chung, \{Sung Kee\} and Kwon, \{Yong Uk\} and Chang, \{Young Tae\} and Sohn, \{Kwang Hoon\} and Shin, \{Jung Han\} and Park, \{Kyu Hwan\} and Hong, \{Bong Jin\} and Chung, \{In Hee\}",

note = "Funding Information: This work was supported by the Korea Science and Engineering Foundation/Center for Biofunctional Molecules and the Ministry of Education/Basic Science Research Institute Fund (98-3437).",

year = "1999",

month = nov,

doi = "10.1016/S0968-0896(99)00183-2",

language = "English",

volume = "7",

pages = "2577--2589",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

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T1 - Synthesis of all possible regioisomers of scyllo-inositol phosphate

AU - Chung, Sung Kee

AU - Kwon, Yong Uk

AU - Chang, Young Tae

AU - Sohn, Kwang Hoon

AU - Shin, Jung Han

AU - Park, Kyu Hwan

AU - Hong, Bong Jin

AU - Chung, In Hee

N1 - Funding Information: This work was supported by the Korea Science and Engineering Foundation/Center for Biofunctional Molecules and the Ministry of Education/Basic Science Research Institute Fund (98-3437).

PY - 1999/11

Y1 - 1999/11

N2 - scyllo-Inositol is the all equatorial stereoisomer of myo-inositol. All possible 12 regioisomers of scyllo-inositol phosphate were synthesized for the first time via a scyllo-inositol benzoate intermediate, which was derived from a myo-inositol derivative. The stereoinversion of myo-inositol into scyllo-inositol was accomplished by Mitsunobu reaction of the vicinal cis- diol. The requisite intermediates, scyllo-inositol benzoates were obtained by benzoyl migration or random benzoylation, and phosphorylated to give scyllo- IP(n). (C) 1999 Elsevier Science Ltd.

AB - scyllo-Inositol is the all equatorial stereoisomer of myo-inositol. All possible 12 regioisomers of scyllo-inositol phosphate were synthesized for the first time via a scyllo-inositol benzoate intermediate, which was derived from a myo-inositol derivative. The stereoinversion of myo-inositol into scyllo-inositol was accomplished by Mitsunobu reaction of the vicinal cis- diol. The requisite intermediates, scyllo-inositol benzoates were obtained by benzoyl migration or random benzoylation, and phosphorylated to give scyllo- IP(n). (C) 1999 Elsevier Science Ltd.

KW - Benzoyl migration

KW - Inositol phosphates

KW - Mitsunobu reaction

KW - scyllo-Inositol

UR - https://www.scopus.com/pages/publications/0033492634

U2 - 10.1016/S0968-0896(99)00183-2

DO - 10.1016/S0968-0896(99)00183-2

M3 - Article

C2 - 10632068

AN - SCOPUS:0033492634

SN - 0968-0896

VL - 7

SP - 2577

EP - 2589

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 11

ER -

Synthesis of all possible regioisomers of scyllo-inositol phosphate

Abstract

Bibliographical note

Keywords

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