512809-23-3

Basic information

• Product Name: benzyl 2-O-benzyl-3,6-dideoxy-α-L-threo-hexopyranosid-4-ulose
• Synonyms: benzyl 2-O-benzyl-3,6-dideoxy-α-L-threo-hexopyranosid-4-ulose
• CAS NO: 512809-23-3
• Molecular Weight: 326.392
• Mol File: 512809-23-3.mol

Chemical Properties

• CAS DataBase Reference: benzyl 2-O-benzyl-3,6-dideoxy-α-L-threo-hexopyranosid-4-ulose(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl 2-O-benzyl-3,6-dideoxy-α-L-threo-hexopyranosid-4-ulose(512809-23-3)
• EPA Substance Registry System: benzyl 2-O-benzyl-3,6-dideoxy-α-L-threo-hexopyranosid-4-ulose(512809-23-3)

Safety Data

• Hazardous Substances Data: 512809-23-3(Hazardous Substances Data)

Upstream product

• 100-51-6 benzyl alcohol 
• 512809-21-1 benzyl 2,3,6-trideoxy-α-L-hex-2-enopyranosid-4-ulose 
• 34819-86-8 3,4-di-O-acetyl-6-deoxy-L-glucal 
• 76404-29-0 phenylmethyl 4-O-acetyl-2,3,6-trideoxy-α-L-erythro-hex-2-enopyranoside 
• 76404-30-3 Benzyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranosid 

Downstream Products

• 512809-26-6 benzyl 2-O-benzyl-4-C-2,5-dimethoxybenzyl-3,6-dideoxy-α-L-ribo-hexopyranoside 

Relevant articles and documents

New chiral pool approach to anthracyclinones. The stereoselective synthesis of idarubicinone

In the present work, a new chiral pool approach has been developed for the synthesis of anthracyclinones. Thus, enone 8, readily available from L-rhamnose, has been converted via addition of 2,5-dimethoxybenzyllithium to the carbonyl group and a series of six reactions into a suitably protected aldehyde 21. The SnCl4-promoted stereospecific cyclization of the latter afforded enantiopure key intermediate 22. Silylation of benzylic hydroxyl of 21 followed by anodic oxidation and selective hydrolysis gave ketoacetals 25 and 26 to which 3-cyano-1(3H)-isobenzofuranone 27 was annelated. Removal of the isopropylidene group in the resulting 28, subsequent oxidation of the C13 hydroxyl and full deprotection led to idarubicinone (4).