108167-80-2

Basic information

• Product Name: isobutyl 3,4-di-O-benzoyl-2,6-dideoxy-β-DL-xylo-hexopyranoside
• Synonyms: isobutyl 3,4-di-O-benzoyl-2,6-dideoxy-β-DL-xylo-hexopyranoside
• CAS NO: 108167-80-2
• Molecular Weight: 412.483
• Mol File: 108167-80-2.mol

Chemical Properties

• CAS DataBase Reference: isobutyl 3,4-di-O-benzoyl-2,6-dideoxy-β-DL-xylo-hexopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: isobutyl 3,4-di-O-benzoyl-2,6-dideoxy-β-DL-xylo-hexopyranoside(108167-80-2)
• EPA Substance Registry System: isobutyl 3,4-di-O-benzoyl-2,6-dideoxy-β-DL-xylo-hexopyranoside(108167-80-2)

Safety Data

• Hazardous Substances Data: 108167-80-2(Hazardous Substances Data)

Upstream product

• 108167-78-8 isobutyl 3,4-anhydro-2,6-dideoxy-β-DL-lyxo-hexopyranoside 
• 108167-77-7 isobutyl 3,4-anhydro-2,6-dideoxy-β-DL-ribo-hexopyranoside 
• 108266-29-1 isobutyl 2,3,6-trideoxy-4-O-(methylsulfonyl)-β-DL-erythro-hexopyranoside 
• 108266-31-5 isobutyl 2,3,4,6-tetradeoxy-β-DL-glycero-hex-3-eno-pyranoside 
• 98-88-4 benzoyl chloride 
• 108167-79-9 isobutyl β-DL-xylo-hexopyranoside 
• 102790-72-7 isobutyl 3,4-anhydro-2,6-dideoxy-α-DL-lyxo-hexopyranoside 
• 102790-76-1 isobutyl 2,6-dideoxy-α-DL-xylo-hexopyranoside 

Relevant articles and documents

Alkaline and Enzymatic Hydrolysis of Isobutyl 3,4-Anhydro-2,6-dideoxy-DL-hexopyranosides. Preparation of Enantiomeric Boivinopyranosides through a Highly Efficient Kinetic Resolution

Racemic isobutyl 3,4-anhydro-2,6-dideoxy-β-ribo-hexopyranoside and -lyxo-hexopyranoside have been prepared starting from the cycloadduct between 3-buten-2-one and isobutyl vinyl ether.Alkaline hydrolysis converted the lyxo isomer exclusively into isobutyl

PREPARATION OF ISOBUTYL 3,4-ANHYDRO-2,6-DIDEOXY-DL-α-LYXO-HEXOPYRANOSIDE AND ITS KINETIC RESOLUTION WITH MICROSOMAL EPOXIDE HYDROLASE.

Racemic isobutyl 3,4-anhydro-2,6-dideoxy-α-lyxo-hexopyranoside, 3, was prepared starting from the cycloadduct between 3-buten-2-one and isobutyl vinyl ether, through a sequence involving hydroboration-oxidation, mesylation, anomeric equilibration, elimination and epoxidation.The intermediate isobutyl 2,3,4,6-tetradeoxy-α-3-DL-hexenopyranoside, 10 was not stable under the conditions used for its preparation (t-BuOK in DMSO), being converted in part into the corresponding 2-hexenopyranoside.Under the same conditions the α-anomer of 10 was stable.Comlete hydrolysis of DL-3 with aqueous NaOH, or with microsomial epoxide hydrolase (MEH) gave exclusively the xylo-diol (isobutyl DL-α-boivinopyranoside 5).When the hydrolylsis with MEH was stopped near 50percent conversion and the product diol was separated from the unchanged epoxide, both were optically active, the former having the L and the latter the D configuration.An ee of at least 96percent was found for both the diol and the epoxide by the use of a chiral shift reagent.