88377-41-7

Basic information

• Product Name: α-(4',6'-Di-O-acetyl-2',3'-dideoxy-α-D-threo-hex-2'-enopyranosyl)acetophenone
• Synonyms: α-(4',6'-Di-O-acetyl-2',3'-dideoxy-α-D-threo-hex-2'-enopyranosyl)acetophenone
• CAS NO: 88377-41-7
• Molecular Weight: 332.353
• Mol File: 88377-41-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: α-(4',6'-Di-O-acetyl-2',3'-dideoxy-α-D-threo-hex-2'-enopyranosyl)acetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: α-(4',6'-Di-O-acetyl-2',3'-dideoxy-α-D-threo-hex-2'-enopyranosyl)acetophenone(88377-41-7)
• EPA Substance Registry System: α-(4',6'-Di-O-acetyl-2',3'-dideoxy-α-D-threo-hex-2'-enopyranosyl)acetophenone(88377-41-7)

Safety Data

• Hazardous Substances Data: 88377-41-7(Hazardous Substances Data)

Upstream product

• 98-86-2 acetophenone 
• 4098-06-0 triacetyl-D-galactal 
• 13735-81-4 1-styrenyloxytrimethylsilane 

Relevant articles and documents

One-pot Mukaiyama type carbon-Ferrier rearrangement of glycals: Application in the synthesis of chromanone 3-C-glycosides

One-pot carbon-Ferrier rearrangement of glycals with unactivated aryl methyl ketones has been developed under mild Silyl triflate catalysis. Keto methyl group of various aryl methyl ketones without being converted into silyl enol ether could directly attack anomeric position of glycals to form keto functionalized C-glycosides in moderate to good yields with high α-selectivity. The versatility of this method has been extended to the synthesis of a small library of chromanone 3-C-glycosides.

Stereocontrolled Routes to Functionalized C-Glycopyranosides

4,6-O-Ethylidene-D-glucopyranose (1) reacts with an acid-washed, stabilized Wittig reagent to give the trans-oct-2-enoate 2 in excellent yield.Cyclization is effected by treatment with dilute base, and after 1 h, a 1:1 mixture of anomers exists which is the optimum concentration of the α-D form.Continuing base treatment for 5 h leads to the β-D anomer exclusively. α-D-C-Glycopyranosides can be obtained as predominant products by Lewis acid catalyzed condensation of acetylated glycals with siloxyalkenes, and anomerization to the β-D forms can be effected with potassium tert-butoxide.For a given pair of these anomers, 1H or 13C NMR pa rameters can be used for assigning configuration α or β.