444183-85-1

Basic information

• Product Name: 4-benzyl-2-C-methyl-D-erythritol
• Synonyms: 4-benzyl-2-C-methyl-D-erythritol
• CAS NO: 444183-85-1
• Molecular Weight: 226.273
• Mol File: 444183-85-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-benzyl-2-C-methyl-D-erythritol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-benzyl-2-C-methyl-D-erythritol(444183-85-1)
• EPA Substance Registry System: 4-benzyl-2-C-methyl-D-erythritol(444183-85-1)

Safety Data

• Hazardous Substances Data: 444183-85-1(Hazardous Substances Data)

Upstream product

• 101020-39-7 (R,R)-4-benzyloxy-2,3-epoxy-2-methylbutanol 

Downstream Products

• 42933-13-1 2-C-methyl-D-erythritol 

Relevant articles and documents

Synthesis of 2-methyl-D-erythritol via epoxy ester-orthoester rearrangement

The biomimetic epoxy ester-orthoester rearrangement has been applied to a new synthesis of 2-methyl-D-erythritol, a branched five-carbon sugar of importance to the deoxyxylulose pathway of isoprenoid biosynthesis. The intermediate orthoacetate is one of the few [2.2.1]-orthoesters to have been reported. Labeling studies with O-18 indicated that this reaction proceeds exclusively via a 5-exo cyclization. NMR analysis of chiral esters indicated an ee of 87% for the starting epoxide and an ee of 86% for the product. This route represents a rapid and convenient method for the synthesis of 2-methyl-D-erythritol and is expected to be useful for generating isotopically labeled intermediates for biochemical studies.