Polysaccharide derivative and separating agent for optical isomer containing the same

Patent metadata

Field	Value
Publication number	US-9499638-B2
Application number	US-201314067419-A
Country	US
Kind code	B2
Filing date	Oct 30, 2013
Priority date	Sep 4, 2006
Publication date	Nov 22, 2016
Grant date	Nov 22, 2016

Abstract

The present invention provides: a polysaccharide derivative containing a structure wherein hydrogen atoms in a hydroxyl group at the 2-position and the 3-position of a structure unit of polysaccharide are substituted with different substituents respectively represented by a specific general formula and a separating agent for optical isomers which contains such a polysaccharide derivative. The present invention can provide a novel polysaccharide derivative which has excellent optical isomer separating ability, making it suitable as a separating agent for optical isomers, and can provide a separating agent for optical isomers which contains the polysaccharide derivative.

First claim

What is claimed is:

1. A method of producing a polysaccharide derivative, comprising the steps of (a) or (b):
(a) modifying a hydroxyl group or amino group at a 2-position of structural units of a polysaccharide with a first substituent represented by a benzoyl group; and
modifying a hydroxyl group or amino group at a 3-position of the structural units with a second substituent represented by the following general formula (II):
—CO—NH—R  (II),

or
(b) modifying a hydroxyl group or amino group at a 2-position of structural units of a polysaccharide with a first substituent represented by a 4-chlorophenylcarbamoyl group; and
modifying a hydroxyl group or amino group at a 3-position of the structural units with a second substituent represented by any one of the following general formulae (I) to (III) and different from the first substituent:
—CO—R  (I)

—CO—NH—R  (II)

—R  (III)

wherein R represents an aliphatic or aromatic hydrocarbon group which may contain a heteroatom, and the group may further have a substituent.

2. The method according to claim 1 , wherein:
the structural units each are a hexose further having a hydroxyl group or amino group at its 6-position; and
the method further comprises the step of protecting the hydroxyl group or amino group at the 6-position with a protective group after modifying the hydroxyl group or amino group at the 2-position.

3. The method according to claim 2 , further comprising the steps of:
removing the protective group at the 6-position after modifying the hydroxyl group or amino group at the 3-position; and
modifying the hydroxyl group or amino group at the 6-position from which the protective group has been removed with a third substituent represented by any one of the general formulae (I) to (III) and different from the second substituent.

4. A method of producing a polysaccharide derivative, comprising:
a 2-position protecting step of protecting a hydroxyl group or amino group at a 2-position of structural units of a polysaccharide with a protective group;
a 3-position modifying step of modifying a hydroxyl group or amino group at a 3-position of the structural units, the 2-position of which has been protected, with a second substituent represented by the following general formula (II) different from the first substituent;
a 2-position deprotecting step of removing the protective group at the 2-position in the structural units, the 3-position of which has been modified; and
a 2-position modifying step of modifying the hydroxyl group or amino group at the 2-position from which the protective group has been removed with a first substituent represented by 4-chlorophenylcarbamoyl group:
—CO—NH—R  (II)

wherein R represents an aliphatic or aromatic hydrocarbon group which may contain a heteroatom, and the group may further have a substituent.

5. The method according to claim 4 , wherein:
the structural units each are a hexose further having a hydroxyl group or amino group at its 6-position; and
the 3-position modifying step is a step of modifying each of the hydroxyl groups or amino groups at both the 3- and 6-positions of the structural units with the second substituent.

6. The method according to claim 5 , wherein:
the 2-position deprotecting step is a step of removing both the protective group at the 2-position and the second substituent at the 6-position; and
the 2-position modifying step is a step of modifying each of the hydroxyl groups or amino groups at both the 2- and 6-positions of the structural units with the first substituent.

7. The method according to claim 4 , wherein:
the structural units each are a hexose further having a hydroxyl group or amino group at its 6-position;
the method further comprises
a 6-position protecting step of protecting the hydroxyl group or amino group at the 6-position of the structural unit, the 2-position of which has been protected, with a protective group before the 3-position modifying step,
a 6-position deprotecting step of deprotecting the protective group at the 6-position in the structural unit the 3-position of which has been modified in the 3-position modifying step before the 2-position deprotecting step, and
a 6-position modifying step of modifying the hydroxyl group or amino group at the 6-position from which the protective group has been removed with a third substituent represented by the same general formula as the general formula of each of the first and second substituents but different from the first and second substituents; and

the 2-position deprotecting step is a step of removing the protective group at the 2-position in the structural unit, the 6-position of which has been modified.

Assignees

• Okamoto Yoshio
• Yamamoto Chiyo
• Kondo Shunsuke
• Kamigaito Masami
• Daicel Corp

Inventors

• Okamoto Yoshio
• Yamamoto Chiyo
• Kondo Shunsuke
• Kamigaito Masami

Classifications

• B01J20/262

  obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. obtained by polycondensation (macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds per se C08G) · CPC title

• B01J20/328

  Polymers on the carrier being further modified · CPC title

• C08B33/02 Primary

  Esters · CPC title

• C07B57/00

  Separation of optically-active compounds · CPC title

• B01J20/3272

  Polymers obtained by reactions otherwise than involving only carbon to carbon unsaturated bonds · CPC title