55832-20-7

Basic information

• Product Name: a-D-Galactopyranoside,3,4-di-O-acetyl-1,6-dichloro-1,6-dideoxy-b-D-fructofuranosyl 4-chloro-4-deoxy-, 2,3,6-triacetate
• Synonyms: a-D-Galactopyranoside,3,4-di-O-acetyl-1,6-dichloro-1,6-dideoxy-b-D-fructofuranosyl 4-chloro-4-deoxy-, triacetate(9CI); 4,1',6'-Trichloro-4,1',6'-trideoxygalactosucrose pentaacetate; Sucralosepentaacetate
• CAS NO: 55832-20-7
• Molecular Formula: C22H29 Cl3 O13
• Molecular Weight: 607.823
• Mol File: 55832-20-7.mol

Chemical Properties

• CAS DataBase Reference: a-D-Galactopyranoside,3,4-di-O-acetyl-1,6-dichloro-1,6-dideoxy-b-D-fructofuranosyl 4-chloro-4-deoxy-, 2,3,6-triacetate(CAS DataBase Reference)
• NIST Chemistry Reference: a-D-Galactopyranoside,3,4-di-O-acetyl-1,6-dichloro-1,6-dideoxy-b-D-fructofuranosyl 4-chloro-4-deoxy-, 2,3,6-triacetate(55832-20-7)
• EPA Substance Registry System: a-D-Galactopyranoside,3,4-di-O-acetyl-1,6-dichloro-1,6-dideoxy-b-D-fructofuranosyl 4-chloro-4-deoxy-, 2,3,6-triacetate(55832-20-7)

Safety Data

• Hazardous Substances Data: 55832-20-7(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 63648-81-7 6-O-acetyl sucrose 
• 35867-25-5 2,3,6,3',4'-pentaacetyl sucrose (6-PAS) 
• 105066-21-5 sucralose-6-acetate 
• 56038-13-2 Sucralose 

Downstream Products

• 56038-13-2 Sucralose 

Relevant articles and documents

THERAPEUTIC AGENTS AND METHODS OF PRODUCING SAME

The present invention relates generally to the field of glycanics and its application to the generation of glycoconjugates for therapeutic use. The present invention also relates to process for the preparation of glycoconjugates.

Process for purification of sucralose

The present invention relates to a process for the purification of Sucralose of formula (I) which comprises acetylation of substantially impure Sucralose to its penultimate intermediate 4,1′,6′-trichloro-4,1′,6′-trideoxy galactosucrose penta-acetate (TOPSA) of formula (VI) followed by purification of TOPSA and then deacetylation of purified TOPSA.

Process to Prepare Sucralose

The present invention relates to a process to prepare sucralose. More particularly the said process relates to the production of sucralose, chemically known as, 6-Dichloro-1,6-dideoxy-β-D-fructofuranosyl-4-chloro-4-deoxy-alpha-D-galactopyranoside of formula (1)

PROCESS FOR THE PREPARATION OF SUCROSE-6-ESTER BY ESTERIFICATION IN THE PRESENCE OF SOLID SUPERACID CATALYST

One embodiment of the present invention is a process of making sucrose-6-ester from sucrose by transesterification in the presence of a solid super acid catalyst such as SO42?—TiO2/Al2O3 or SO42?—TiO2. The sucrose-6-acetate is then chlorinated to afford sucralose-6-acetate, using BTC or thionyl chloride. Sucralose-6-acetate is converted into TPSGA for the purpose of purification. TPSGA is de-esterified by sodium methoxide/methanol or sodium ethoxide/ethanol to give sucralose.

Novel chlorination process for preparing sucralose

A process for preparing a sucralose-6-ester, a key intermediate to sucralose. The process contains (a) creating a heterogeneous mixture comprising a first phase comprising a sucrose-6-ester and a second phase comprising a chlorinating reagent; and (b) reacting the sucrose-6-ester with the chlorinating reagent, to prepare a sucralose-6-ester. In addition, processes for preparing sucralose from sucrose-6-esters are provided.

PROCESS FOR THE PREPARATION OF A GLUCOSE DERIVATIVE

The present invention relates to an improved, safe, commercially viable, cost effective and eco friendly process for the preparation of 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose (Sucralose). The invention is directed towards the convenient synthesis of 2,3,4,3',4'-penta-O-acetyl sucrose (4-PAS) from 6,1',6'-tri-O-trityl-penta-O-acetyl sucrose ("TRISPA").

Synthesis, structure and sweetness of 4-chloro-4-deoxy-α-d-galactopyranosyl 1,4,6-trichloro-1,4,6-trideoxy-β-d-tagatofuranoside

The reaction of 6-O-acetylsucrose with sulfuryl chloride was reexamined. The major product, after dechlorosulfation and acetylation, was determined by X-ray diffraction to be 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-α-D-galactopyranosyl 3-O-acetyl-1,4,6-trichloro-1,4,6-trideoxy-β-D-tagatofuranoside and not the corresponding sorbofuranoside, as reported earlier. The mechanism of chlorination at C-4′ is discussed. The intensity of sweetness of the free 4′-chlorodeoxy tagato isomer is determined to be only about one-tenth the sweetness of the corresponding chlorodeoxy fructo isomer, which strongly suggests that the hydrophobic γ-site is located at C-4′.

Selected removal of trityl groups from trispa

2,3,4,3',4'-penta-O-acetyl sucrose (4-PAS), a key intermediate in the preparation of sucralose, is prepared by the selective removal of trityl groups from 6,1', 6'-tri-O-trityl-penta-O-acetyl sucrose (TRISPA) in which a catalytic amount of an aralkyl chloride or hydrogen chloride is added to a solution of TRISPA is an inert organic solvent is hydrogenated in the presence of a hydrogenolysis catalyst such a platinum or palladium.

SYNTHESIS OF AN INTENSELY SWEET CHLORODEOXYSUCROSE: MECHANISM OF 4'-CHLORINATION OF SUCROSE BY SULPHURYL CHLORIDE

Reaction of 6-acetylsucrose with sulphuryl chloride in chloroform-pyridine affords, after dechlorosulphation and acetylation, a mixture of two isomeric 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-α-D-galactopyranosyl 3-O-acetyl-1,4,6,-trichloro-1,4,6-trideoxy-β-D-hexulofuranosides (6 and 7) and 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-α-D-galactopyranosyl 3,4-di-O-acetyl-1,6-dichloro-1,6-dideoxy-β-D-fructofuranoside (4).Chlorination of C-4, C-1', and C-6' occurs by direct displacement of the initially formed chlorosulphonyloxy groups by chloride ions, but displacement of the 4'-chlorosulphate is sterically hindered.The introdution of a 4'-chloro substituent involves ring opening of intermediate 3',4'-epoxides by chloride ions, the ribo-epoxide producing the sorbo-isomer 6 and the lyxo-epoxide giving the fructo-isomer 7.The proposed mechanism is supported by the formation of 4-chloro-4-deoxyfructofuranosides when 3',4'-lyxo-hexulofuranosides are treated with sulphuryl chloride under the same conditions.

Process for the preparation of 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose

4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose is prepared by a process including the steps of: (a) isomerizing 2,3,4,3',4'-penta-O-acetyl sucrose to 2,3,6,3',4'-penta-O-acetyl sucrose; (b) chlorinating the isomerized acetate at the 4,1' and 6'-positions; and (c) deacetylating the resulting chlorinated product; the isomerization step (a) being effected by treating a solution of 2,3,4,3',4'-penta-O-acetyl sucrose in an inert solvent with a weak acid at an elevated temperature.