639504-92-0

Basic information

• Product Name: methyl 2,3,4-tri-O-benzyl-6-deoxy-6-iodo-β-D-glucopyranoside
• Synonyms: methyl 2,3,4-tri-O-benzyl-6-deoxy-6-iodo-β-D-glucopyranoside
• CAS NO: 639504-92-0
• Molecular Weight: 574.456
• Mol File: 639504-92-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: methyl 2,3,4-tri-O-benzyl-6-deoxy-6-iodo-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,4-tri-O-benzyl-6-deoxy-6-iodo-β-D-glucopyranoside(639504-92-0)
• EPA Substance Registry System: methyl 2,3,4-tri-O-benzyl-6-deoxy-6-iodo-β-D-glucopyranoside(639504-92-0)

Safety Data

• Hazardous Substances Data: 639504-92-0(Hazardous Substances Data)

Upstream product

• 101312-02-1 methyl 2,3-di-O-benzyl-4,6-di-O-benzylidene-β-D-glucopyranoside 
• 4356-80-3 methyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside 

Downstream Products

• 1461750-25-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one 
• 639504-89-5 5-(methyl 2,3,4-tri-O-benzyl-6-deoxy-β-D-glucopyranos-6-yl)tetrazole 
• 639504-87-3 methyl 2,3,4-tri-O-benzyl-6-cyano-6-deoxy-β-D-glucopyranoside 
• 189222-29-5 methyl tri-O-benzyl-6-deoxy-β-D-xylo-hex-5-enopyranoside 
• 189222-28-4 (1S,2S,3S,4R,5R)-2,3,4-tri-O-benzyl-1-O-methylcyclohexane-1,2,3,4,5-pentol 

Relevant articles and documents

Vinyl Grignard-Mediated Stereoselective Carbocyclization of Lactone Acetals

A novel Ferrier-type carbocyclization is reported. It involves a carbohydrate-derived lactone acetal synthesized from methyl α-d-glucopyranoside, which upon treatment with excess vinylmagnesium bromide provides a highly substituted carbocyclic product as a single stereoisomer. The yield is greatly increased when N,N,N′,N′-tetramethylethylenediamine is added to the reaction mixture. Optimized reaction conditions have been applied to lactone acetals derived from other carbohydrates. Based on the obtained results, a possible reaction mechanism has been proposed. Furthermore, scalability of the reaction up to 15 g scale and derivatization of the carbocyclic product has been demonstrated, including the formation of a rare trans-bicyclo[4.3.0]nonene scaffold via a ring-closing metathesis. The structure of this and all carbocyclic products were confirmed by X-ray crystallographic analysis.

Novel carbocyclic ring closure of hex-5-enopyranosides

Retention of configuration at the anomeric carbon atom is observed for a novel rearrangement of carbohydrates. The readily accessible vinyl acetal 1 undergoes a triisobutylaluminum-assisted, stereoselective transposition of an oxygen atom on the ring with