Compound useful for manufacturing salacinol, method for manufacturing the compound, method for manufacturing salacinol, methods for protecting and deprotecting diol group, and protective agent for diol group

Patent metadata

Field	Value
Publication number	US-10059686-B2
Application number	US-201715709794-A
Country	US
Kind code	B2
Filing date	Sep 20, 2017
Priority date	Mar 20, 2014
Publication date	Aug 28, 2018
Grant date	Aug 28, 2018

Abstract

An object of the present invention is to provide a novel compound useful for manufacturing salacinol, a method for manufacturing the compound, a method for manufacturing salacinol, methods for protecting and deprotecting a diol group, and a protective agent for a diol group. A compound represented by Formula (1) is a compound useful for manufacturing salacinol.

(In the formula, each of R 1a and R 1b is a hydrogen atom or a hydroxy protective group; R 2 is a hydroxy group or the like; and R 3 is a hydroxy group or the like.).

First claim

What is claimed is:

1. A method for manufacturing salacinol, comprising: obtaining a compound represented by Formula (1b) by reacting a compound represented by Formula (1a) with a compound represented by Formula (7),

(in the formula, each of R 1a and R 1b are the same as or different from each other and each represent a hydrogen atom or a carboxy protective group),

(in the formula, each of R 4a , R 4b , and R 4c are the same as or different from each other and each represent a hydrogen atom or a hydroxy protective group), and

(in the formula, each of R 1a , R 1b , R 4a , R 4b , and R 4c has the same definition as described above); and then
subjecting the compound represented by Formula (1b) to a deprotection reaction.

2. The manufacturing method according to claim 1 ,
wherein each of R 1a and R 1b is a carboxy protective group, and each of R 4a , R 4b , and R 4c is a hydrogen atom.

3. A method for manufacturing salacinol, comprising: obtaining a compound represented by Formula (1c) by reacting a compound represented by Formula (8) with a compound represented by Formula (9),

(in the formula, R 5 is an aryl group which may be substituted),

(in the formula, R 1a and R 1b are the same as or different from each other and each represent a hydrogen atom or a carboxy protective group; R 6 is a C 1-6 alkyl group which may be substituted), and

(in the formula, each of R 1a , R 1b , and R 5 has the same definition as described above);
then obtaining a compound represented by Formula (1d) by subjecting the compound represented by Formula (1c) to a deprotection reaction,

(in the formula, each of R 1a and R 1b has the same definition as described above);
then obtaining a compound represented by Formula (1a) by reacting the compound represented by Formula (1d) with a sulfur-containing compound and then subjecting the resulting compound to an oxidation reaction if necessary,

(in the formula, each of R 1a and R 1b has the same definition as described above);
then obtaining a compound represented by Formula (1b) by reacting the compound represented by Formula (1a) with a compound represented by Formula (7),

(in the formula, R 4a , R 4b , and R 4c are the same as or different from each other and each represent a hydrogen atom or a hydroxy protective group), and

(in the formula, each of R 1a , R 1b , R 4a , R 4b , and R 4c has the same definition as described above); and then
subjecting the compound represented by Formula (1b) to a deprotection reaction.

4. The manufacturing method according to claim 3 ,
wherein R 5 is a phenyl group which may be substituted.

5. The manufacturing method according to claim 3 ,
wherein each of R 1a and R 1b is a carboxy protective group, and each of R 4a , R 4b , and R 4c is a hydrogen atom.

Assignees

• Fujifilm Corp

Inventors

• Nakamura Koki
• Nagase Hisato
• FUJINO Yuuta
• Watanabe Katsuyuki
• Katsumata Taiji

Classifications

• C07D319/06

  not condensed with other rings · CPC title

• Y02P20/55

  Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups · CPC title

• C07D317/30

  Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title

• C07D409/06

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• C07D333/32

  Oxygen atoms · CPC title