Triazole linked carbohydrates

• US 6,852,866 B2
• Filed: 08/15/2003
• Issued: 02/08/2005
• Est. Priority Date: 09/02/1999
• Status: Expired due to Fees

• Current Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: Sabesan, Subramaniam
• Primary Examiner(s): Tsang, Cecilia J.
• Assistant Examiner(s): Covington, Raymond
• Application Number:
  US10/641,448
• Publication Number:
  US 20040059105A1
• Time in Patent Office: 543 Days
• Field of Search: 549/420, 549/478, 549/417, 549/419, 549/480
• US Class Current: 549/420
• CPC Class Codes: C07H 13/10 having the esterifying carboxyl radicals directly attached to heterocyclic rings
• CPC Class Codes: C07H 15/26 Acyclic or carbocyclic radicals, substituted by hetero rings
• CPC Class Codes: C07H 19/056 Triazole or tetrazole radicals

Abstract

Disclosed is an invention concerning triazolyloligosaccharides, oligosaccharides wherein the bonding between the saccharide groups is via a triazole group and methods for their preparation.

Claims

1. A process for the preparation of a compound having the structure I,

wherein each R, independently, is selected from the group consisting of hydrogen, hydroxy, alkoxy having up to 8 carbon atoms, acyloxy having up to 8 carbon atoms, acylamino having up to 8 carbon atoms, C₁ to C₂₀ hydrocarbyl and substituted hydrocarbyl and amino;

R³ is selected from the group consisting of H, C₁ to C₂₀ hydrocarbyl and substituted hydrocarbyl;

m is 0 or 1, and

n and n′

are, independently, 4 or 5, comprising;

contacting azides of the structure IA;

wherein R is selected from the group consisting of hydrogen, hydroxy, alkoxy having up to 8 carbon atoms, acyloxy having up to 8 carbon atoms, acylamino having up to 8 carbon atoms, C₁ to C₂₀ hydrocarbyl or substituted hydrocarbyl and amino;

n is 4 or 5, and m is 0 or 1,

with compounds of the structure IB

wherein R is as described above and R³ is selected from the group consisting of H, C₁ to C₂₀ hydrocarbyl and substituted hydrocarbyl; and

n′

is 4 or 5.

2. A process according to claim 1 for the preparation of triazolyldisaccharides of the structure II,

wherein R¹ is selected from the group consisting of H, Na, C₁-C₂₀ alkyl,

wherein R² is selected from the group consisting of hydroxy,

alkoxy having from 1 to 8 carbon atoms, acyloxy having from 1 to 8 carbon atoms, acylamino having from 1 to 8 carbon atoms, amino, hydrogen, and guanidino;

wherein R³ is selected from the group consisting of H, C₁ to C₂₀ hydrocarbyl, and substituted hydrocarbyl;

wherein R⁴ is selected from the group consisting of H, acyl having from 1 to 8 carbon atoms, and alkyl having 1 to 20 carbon atoms;

wherein R⁶ and R^6′

are selected from the group consisting of H, OH, C₁ to C₂₀ alkoxy, C₁ to C₂₀ substituted alkoxy, mono-, di- or oligosaccharide, and alkylideneoxy taken together with R^7′

when R^7′

is not H, provided that one of R⁶ and R^6′

must be H but R⁶ and R^6′

may not both be H; and

R⁷ and R^7′

are selected from the group consisting of H, acyl having from 1 to 8 carbon atoms, C₁ to C₂₀ alkyl, aryl, and alkylidene taken together with an adjacent R⁶, R^6′

, R⁷ and R^7′

;

comprising contacting compounds of the structure IIA;

wherein R¹ is selected from the group consisting of H, Na, and C₁-C₂₀ alkyl,

R² is selected from the group consisting of hydroxy, alkoxy having from 1 to 8 carbon atoms, acyloxy having from 1 to 8 carbon atoms, acylamino having from 1 to 8 carbon atoms, amino, hydrogen, and guanidino;

R³ is selected from the group consisting of H, C₁ to C₂₀ hydrocarbyl and substituted hydrocarbyl; and

R⁴ is selected from the group consisting of H, acyl having from 1 to 8 carbon atoms and alkyl having 1 to 20 carbon atoms;

with compounds of the structure IIB

wherein R³ is selected from the group consisting of H, C₁ to C₂₀ hydrocarbyl and substituted hydrocarbyl;

R⁶ and R^6′

are selected from the group consisting of H, OH, C₁ to C₂₀ alkoxy and substituted alkoxy, mono-, di- or oligosaccharide, and alkylideneoxy taken together with R^7′

when R^7′

is not H, provided that one of R⁶ and R^6′

must be H but R⁶ and R^6′

may not both be H; and

R⁷ and R^7′

are selected from the group consisting of H, acyl having from 1 to 8 carbon atoms, C₁ to C₂₀ alkyl, aryl, and alkylidene taken together with an adjacent R⁶, R^6′

, R⁷ and R^7′

.

3. A process according to claim 1 for the preparation of a compound of the structure III,

wherein R³ is selected from the group consisting of H, C₁ to C₂₀ hydrocarbyl, and C₁ to C₂₀ substituted hydrocarbyl;

wherein R⁸ is selected from the group consisting of H, alkyl having from 1 to 20 carbon atoms, and acyl having from 1 to 8 carbon

atoms;

wherein R⁶ and R^6′

are selected from the group consisting of H, OH, C₁ to C₂₀ alkoxy, C₁ to C₂₀ substituted alkoxy, mono-, di- or oligosaccharide, and alkylideneoxy taken together with R^7′

, when R^7′

is not H, provided that one of R⁶ and R^6′

must be H but R⁶ and R^6′

may not both be H; and

wherein R⁷ and R^7′

are selected from the group consisting of H, acyl having from 1 to 8 carbon atoms, C₁ to C₂₀ alkyl, aryl, and alkylidene taken together with an adjacent R⁶, R^6′

, R⁷ or R^7′

,

comprising;

contacting a compound of the structure IIIA;

wherein R⁸ is selected from the group consisting of H, alkyl, wherein the alkyl having from 1 to 20 carbon atoms, and acyl, where the acyl group contains from 1 to 8 carbon atoms;

with compounds of the structure IIB,

wherein R³ is selected from the group consisting of H C₁ to C₂₀ hydrocarbyl and substituted hydrocarbyl;

R⁶ and R^6′

are selected from the group consisting of H, OH, C₁ to C₂₀ alkoxy and substituted alkoxy, mono-, di- or oligosaccharide, and alkylideneoxy taken together with R^7′

when R^7′

is not H, provided that one of R⁶ and R^6′

must be H but R⁶ and R^6′

may not both be H; and

R⁷ and R^7′

are selected from the group consisting of H, acyl having from 1 to 8 carbon atoms, C₁ to C₂₀ alkyl, aryl, and alkylidene taken together with an adjacent R⁶, R^6′

, R⁷ and R^7′

.

4. Acetylenic compounds of the structure IB

wherein R is selected from the group consisting of hydrogen, hydroxy, alkoxy having up to 8 carbon atoms, acyloxy having up to 8 carbon atoms, acylamino having up to 8 carbon atoms, C₁ to C₂₀ hydrocarbyl, substituted hydrocarbyl and amino;

R³ is selected from the group consisting of H, C₁ to C₂₀ hydrocarbyl and substituted hydrocarbyl; and

n′

is 5.

5. Acetylenic compounds according to claim 4 of the structure IIB

wherein R³ is selected from the group consisting of H, C₁ to C₂₀ hydrocarbyl and substituted hydrocarbyl;

R⁶ and R^6′

are selected from the group consisting of H, OH, C₁ to C₂₀ alkoxy and substituted alkoxy, mono-, di- or oligosaccharide, and alkylideneoxy taken together with R^7′

when R^7′

is not H, provided that one of R⁶ and R^6′

must be H but R⁶ and R^6′

may not both be H; and

R⁷ and R^7′

are selected from the group consisting of H, acyl having from 1 to 8 carbon atoms, C₁ to C₂₀ alkyl, aryl, and alkylidene taken together with an adjacent R⁶, R^6′

, R⁷ and R^7′

.