Cyclic Sulfamidite as Simultaneous Protecting Group for Amino Alcohols: Development of a Mild Deprotection Protocol Using Thiophenol

Juri Sakata; Kazunari Akita; Manabu Sato; Masashi Shimomura; Hidetoshi Tokuyama

doi:10.1248/CPB.C20-00531

Cyclic Sulfamidite as Simultaneous Protecting Group for Amino Alcohols: Development of a Mild Deprotection Protocol Using Thiophenol

Juri Sakata, Kazunari Akita, Manabu Sato, Masashi Shimomura, Hidetoshi Tokuyama

PHA - Molecular Pharmaceutical Science

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

Abstract

This study describes the novel utility of cyclic sulfamidite as a simultaneous protecting group for 1,2- or 1,3-amino alcohols. An exceptionally mild and neutral condition for the removal of the cyclic sulfamidite was developed. The deprotection condition demonstrated a broad range of functional-group compatibility, including a substrate bearing a Z-enyne structure without any loss of double-bond stereochemistry.

Original language	English
Pages (from-to)	996-1000
Number of pages	5
Journal	Chemical and Pharmaceutical Bulletin
Volume	68
Issue number	10
DOIs	https://doi.org/10.1248/CPB.C20-00531
Publication status	Published - 2020

Keywords

Amino alcohol
Cyclic sulfamidite
Deprotection
Protecting group
Protection

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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10.1248/CPB.C20-00531

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abstract = "This study describes the novel utility of cyclic sulfamidite as a simultaneous protecting group for 1,2- or 1,3-amino alcohols. An exceptionally mild and neutral condition for the removal of the cyclic sulfamidite was developed. The deprotection condition demonstrated a broad range of functional-group compatibility, including a substrate bearing a Z-enyne structure without any loss of double-bond stereochemistry.",

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author = "Juri Sakata and Kazunari Akita and Manabu Sato and Masashi Shimomura and Hidetoshi Tokuyama",

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AU - Sato, Manabu

AU - Shimomura, Masashi

AU - Tokuyama, Hidetoshi

PY - 2020

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AB - This study describes the novel utility of cyclic sulfamidite as a simultaneous protecting group for 1,2- or 1,3-amino alcohols. An exceptionally mild and neutral condition for the removal of the cyclic sulfamidite was developed. The deprotection condition demonstrated a broad range of functional-group compatibility, including a substrate bearing a Z-enyne structure without any loss of double-bond stereochemistry.

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KW - Cyclic sulfamidite

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KW - Protecting group

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Cyclic Sulfamidite as Simultaneous Protecting Group for Amino Alcohols: Development of a Mild Deprotection Protocol Using Thiophenol

Abstract

Keywords

ASJC Scopus subject areas

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