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EP0220907A2 Expired / Lapsed EP ⏱️ 0.0 years remaining

Process for the preparation of 1,6-dichloro-1,6-dideoxy-beta-D-fructofuranosyl-4-chloro-4-deoxy-alpha-galactopyranoside

Assignee: Janssen Pharmaceuticals Inc
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Filing: 1986-10-20
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Granted: —
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Expires: 2006-10-20
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Abstract

Abstract A process for the preparation of 1,6-dichloro-1,6-­dideoxy-β-D-fructofuranosyl-4-chloro-4-deoxy-α-galacto­pyranoside comprising the steps of (a) reacting sucrose with a tritylating agent; (b) acetylating the tritylated reaction product; (c) detritylating the acetylated reaction product; (d) isomerizing the resulting penta-acetate; (e) chlorinating the isomerized product; and (f) deacetylating the chlorinated reaction product.

Inventors

  • 👤 William Tully
  • 👤 Nicholas M. Vernon
  • 👤 Peter A. Walsh

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-07 02:27
CPC Classifications
A; A23; A23L; A23L27/00; C; C07; C07H; C07H5/00; C07H5/02; C07H13/00; C07H13/02; C07H13/04

Claims Analysis

Total Claims: 8
Claim 1
Independent Claim 18 words
A process for the preparation of 2,3,6,3',4'-penta-O-­acetylsucrose comprising isomerizing 2,3,4,3',4'-penta-­O-acetylsucrose in a non-aqueous solvent with a weak base.
Claim 2
Dependent Claim 18 words
A process for the preparation of 2,3,6,3',4'-penta-O-­acetylsucrose comprising isomerizing 2,3,4,3',4'-penta-­O-acetylsucrose in a non-aqueous solvent with a weak base.
Claim 3
Dependent Claim 28 words
A process according to Claim 1 wherein the weak base is selected from the group consisting of tert-butylamine, triethylamine, pyrrolidine, di-N-propylamine, di-isopropylamine, morpholine, n-butylamine, isopropylamine, piperidine and diethylamine.
Claim 4
Dependent Claim 12 words
A process according to Claim 2 wherein the weak base is tert-butylamine.
Claim 5
Dependent Claim 23 words
A process according to any one of claims 1 to 3 which is carried out at a temperature of from 30°C to 60°C.
Claim 6
Dependent Claim 73 words
A process for the preparation of 1,6-dichloro-1,6-dideoxy-β-D-fructofuranosyl-4-chloro-4-­deoxy-α-galactopyranoside comprising the steps of: (a) reacting sucrose with a tritylating agent; (b) acetylating the tritylated reaction product with an acetylating agent to obtain 6,1',6'-tri-O-­tritylsucrose penta-acetate; (c) detritylating the 6,1',6'-tri-O-tritylsucrose penta-acetate to obtain 2,3,4,3',4'-penta-O-­acetylsucrose; (d) isomerizing the 2,3,4,3',4'penta-O-acetyl­ sucrose using a process according to any one of claims 1 to 4 to obtain 2,3,6,3',4'-penta-O-acetylsucrose; (e) chlorinating 2,3,6,3',4'-penta-O-acetylsucrose to obtain 4,1',6'-trichloro-4,1',6'-trideoxy­galactosucrose pentaacetate; and (f) deacetylating the chlorinated product.
Claim 7
Dependent Claim 16 words
A process according to claim 5 wherein the tri­tylating agent in step (a) is trityl chloride.
Claim 8
Dependent Claim 19 words
A process according to claim 5 or claim 6 wherein the acetylating agent in step (b) is acetic anhydride.

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