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-9802913-B2
Application number	US-201615268829-A
Country	US
Kind code	B2
Filing date	Sep 19, 2016
Priority date	Mar 20, 2014
Publication date	Oct 31, 2017
Grant date	Oct 31, 2017

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 compound represented by Formula (1),

(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; and each of R 2 and R 3 is a hydroxy group, R 2 is a group represented by Formula (2) and R 3 is a group represented by Formula (3),

(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 * represents a binding position), and

(in the formula, * has the same definition as described above),

or R 2 and R 3 are bonded to each other and represent a group represented by Formula (4),
*—O—X 1 —O—*  (4)

(in the formula, X 1 is a group represented by Formula (5) or a group represented by Formula (6); and * has the same definition as described above),

(in the formula, R 5 is an aryl group which may be substituted; and * has the same definition as described above), and

(in the formula, * has the same definition as described above)).

2. The compound according to claim 1 ,
wherein R 1a and R 1b are the same as or different from each other and each represent a carboxy protective group.

3. The compound according to claim 1 ,
wherein each of R 2 and R 3 is a hydroxy group.

4. The compound according to claim 1 ,
wherein R 2 is a group represented by Formula (2); and R 3 is a group represented by Formula (3),

(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 * is a binding position), and

(in the formula, * has the same definition as described above).

5. The compound according to claim 1 ,
wherein R 2 and R 3 are bonded to each other and represent a group represented by Formula (4),
*—O—X 1 —O—*  (4)

(in the formula, X 1 is a group represented by Formula (5) or (6); and * has the same definition as described above),

(in the formula, R 5 is an aryl group which may be substituted; and * is a binding position), and

(in the formula, * has the same definition as described above).

6. The compound according to claim 1 ,
wherein R 5 is a phenyl group which may be substituted.

7. The compound according to claim 1 that is a compound selected from dimethyl 2-((4aS,8aR)-6-phenyltetrahydro[1,3]dioxino[5,4-d][1,3]dioxin-2-yl)malonate, dimethyl 2-((4R,5S)-5-hydroxy-4-(hydroxymethyl)-1,3-dioxan-2-yl)malonate, dimethyl 2-((4aR,8aS)-2,2-dioxidotetrahydro[1,3]dioxin[5,4-d][1,3,2]dioxathiin-6-yl)malonate, (4S,5S)-4-(((2R,3 S,4S)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydro-1H-thiophen-1-ium-1-yl) methyl-2-(1,3-dimethoxy-1,3-dioxopropan-2-yl)-1,3-dioxan-5-yl sulfate, (4S,5 S)-4-(((1 S,2R,3 S,4S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)tetrahydro-1H-thiophen-1-ium-1-yl)methyl)-2-(1,3-dimethoxy-1,3-dioxopropan-2-yl)-1,3-dioxan-5-yl sulfate, (4S,5S)-4-(((1 S,2R,3 S,4S)-3,4-bis((4-methoxybenzyl)oxy)-2-(((4-methoxybenzyl)oxy)methyl)tetrahydro-1H-thiophen-1-ium-1-yl)methyl)-2-(1,3-dimethoxy-1,3-dioxopropan-2-yl)-1,3-dioxan-5-yl sulfate, diethyl 2-((4aS,8aR)-6-phenyltetrahydro[1,3]dioxino[5,4-d][1,3]dioxin-2-yl)malonate, diethyl 2-((4R,5S)-5-hydroxy-4-(hydroxymethyl)-1,3-dioxan-2-yl)malonate, diethyl 2-((4aR,8aS)-2,2-dioxidotetrahydro[1,3]dioxino[5,4-d][1,3,2]dioxathiin-6-yl)malonate, and (4S,5S)-2-(1,3-diethoxy-1,3-dioxopropan-2-yl)-4-(((2R,3 S,4S)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydro-1H-thiophen-1-ium-1-yl)methyl)-1,3-dioxan-5-yl sulfate.

Assignees

• Fujifilm Corp

Inventors

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

Classifications

• C07D493/04

  Ortho-condensed systems · CPC title

• C07D333/46 Primary

  substituted on the ring sulfur atom · CPC title

• C07D333/32

  Oxygen atoms · CPC title

• C07D497/04

  Ortho-condensed systems · CPC title

• C07D409/06

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