19685-14-4

Basic information

• Product Name: 6-chloro-O¹,O²;O³,O⁵-diisopropylidene-α-D-6-deoxy-glucofuranose
• Synonyms: 6-chloro-O¹,O²;O³,O⁵-diisopropylidene-α-D-6-deoxy-glucofuranose
• CAS NO: 19685-14-4
• Molecular Weight: 278.733
• Mol File: 19685-14-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 6-chloro-O¹,O²;O³,O⁵-diisopropylidene-α-D-6-deoxy-glucofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 6-chloro-O¹,O²;O³,O⁵-diisopropylidene-α-D-6-deoxy-glucofuranose(19685-14-4)
• EPA Substance Registry System: 6-chloro-O¹,O²;O³,O⁵-diisopropylidene-α-D-6-deoxy-glucofuranose(19685-14-4)

Safety Data

• Hazardous Substances Data: 19685-14-4(Hazardous Substances Data)

Upstream product

• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 40656-44-8 6-chloro-6-deoxy-D-glucose 
• 59865-23-5 (2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid 
• 131156-46-2 tert-Butyl-diphenyl-[(R)-3-((3aR,5R,6R,6aR)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-butoxy]-silane 
• 127223-28-3 (3aR,5R,6S,6aR)-5-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol 

Relevant articles and documents

The mechanism of the hydroxyl → halogen exchange reaction in the presence of triphenylphosphine, N-bromosuccinimide, and N,N-dimethylformamide: Application of a new Vilsmeier-type reagent in carbohydrate chemistry

Triphenylphosphine reacts with N-bromosuccinimide to give a phosphonium salt (13), which reacts with N,N-dimethylformamide to afford N,N-dimethylsuccinimidomethaniminium bromide (16). The latter product reacts with an alcohol to give an O-formiminium compound 17, and, in the presence of an alcohol, 13 is transformed into an alkoxyphosphonium intermediate (14). Both 4 and 17 can be converted by heating into an alkyl bromide. Hydrolysis of 17 gives the corresponding O-formyl derivative. Reaction of 1.2:5.6-di-O-isopropylidene-α-D-glucofuranose with 13 or 16 gave 6-bromo-6-deoxy-1,2:3,5-di-O-isopropylidene-α-D-glucofuranose and a possible mechanism for these reactions is suggested. An efficient method for the preparation of 3-deoxy-3-halogeno-1,2:5,6-di-O-isopropylidene-α-D-allofuranose derivatives and a new procedure for selective O-formylation are described.