19465-09-9

Basic information

• Product Name: methyl 4,6-O-benzylidene-2-bromo-2-deoxy-α-D-altropyranoside
• Synonyms: methyl 4,6-O-benzylidene-2-bromo-2-deoxy-α-D-altropyranoside
• CAS NO: 19465-09-9
• Molecular Weight: 345.19
• Mol File: 19465-09-9.mol

Chemical Properties

• CAS DataBase Reference: methyl 4,6-O-benzylidene-2-bromo-2-deoxy-α-D-altropyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4,6-O-benzylidene-2-bromo-2-deoxy-α-D-altropyranoside(19465-09-9)
• EPA Substance Registry System: methyl 4,6-O-benzylidene-2-bromo-2-deoxy-α-D-altropyranoside(19465-09-9)

Safety Data

• Hazardous Substances Data: 19465-09-9(Hazardous Substances Data)

Upstream product

• 2880-96-8 methyl 2,3-anhydro-4,6-oxy-benzylidene-β-D-mannopyranoside 
• 3150-15-0 methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside 
• 925-90-6 ethylmagnesium bromide 

Downstream Products

• 5987-33-7 4,6-O-benzylidene-D-allal 
• 16718-95-9 methyl 4,6-O-benzylidene-2-deoxy-α-D-altropyranoside 

Relevant articles and documents

Synthesis of 2-C- and 3-C-aryl pyranosides

Lithium diphenylcuprate treatment of methyl 2,3-anhydro-4,6-O-benzylidene-D-pyranosides in which the anomeric substituent and the three-membered rings are cis oriented furnished the expected trans-diaxial opening products. When the relationship between the anomeric group and the epoxide was trans, the same experimental conditions led only to recovered starting material. Cyano cuprates of the type R2CuCNLi2 added stereoselectively to carbohydrate ketones at C-2 and C-3 from the opposite side relative to the anomeric substituent.

Regiocontrolled Opening of Cyclic Ethers Using Dimethylboron Bromide

The cleavage of various cyclic ethers (3- to 7-membered rings) was achieved under very mild conditions using dimethylboron bromide to afford the corresponding bromo alcohols.In particular, 2-substituted tetrahydrofurans were regioselectively cleaved by a predominantly SN2 - type mechanism favoring the formation of primary vs. secondary bromides.Dimethylboron bromide also cleaved chemoselectively substituted tetrahydrofurans in the presence of functional groups such as acyclic ethers, silyl ethers, esters, amides, ketones,etc.

A CONVENIENT METHOD FOR THE PREPARATION OF 4,6-O-BENZYLIDENEGLYCALS FROM METHYL 2,3-ANHYDRO-4,6-O-BENZYLIDENE-α-D-HEXAPYRANOSIDES

The reaction of methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside (1) with ethylmagnesium bromide in the presence of CuI afforded 4,6-O-benzylidene-1,2-dideoxy-D-ribo-hex-1-enopyranoside (2).Similarly, methyl 2,3-anhydro-4,6-O-benzylidene-α-D-gulopy