78699-85-1

Basic information

• Product Name: 2,3,4,5,6-penta-O-benzyl-aldehydo-D-glucose
• Synonyms: 2,3,4,5,6-penta-O-benzyl-aldehydo-D-glucose
• CAS NO: 78699-85-1
• Molecular Weight: 630.781
• Mol File: 78699-85-1.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 2,3,4,5,6-penta-O-benzyl-aldehydo-D-glucose(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,5,6-penta-O-benzyl-aldehydo-D-glucose(78699-85-1)
• EPA Substance Registry System: 2,3,4,5,6-penta-O-benzyl-aldehydo-D-glucose(78699-85-1)

Safety Data

• Hazardous Substances Data: 78699-85-1(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 50-99-7 D-glucose 
• 1941-52-2 D-glucose diethyl mercaptal 
• 2280-44-6 D-Glucose 
• 115704-95-5 2,3,4,5,6-penta-O-benzyl-D-glucose diethyl dithioacetal 
• 53282-12-5 ethyl (E)-3-(2-furyl)prop-2-enoate 
• 221015-54-9 tert-Butyl-dimethyl-((1S,2S,3S,4S,5S,7R)-2,3,4-tris-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-7-ylmethoxy)-silane 
• 221015-58-3 (1R,2S,3S,4S,5R,7S)-2,3,4-Tris-benzyloxy-7-iodomethyl-6,8-dioxa-bicyclo[3.2.1]octane 
• 221015-56-1 ((1S,2S,3S,4S,5S,7R)-2,3,4-Tris-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-7-yl)-methanol 
• 221015-52-7 (1S,2S,3R,4S,5S,7R)-2-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxymethyl)-6,8-dioxa-bicyclo[3.2.1]octane-3,4-diol 
• 221015-50-5 ((1R,2S,5S,7R)-2-Benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-3-en-7-ylmethoxy)-tert-butyl-dimethyl-silane 
• 221015-44-7 (1S,2R)-3-(tert-Butyl-dimethyl-silanyloxy)-1-furan-2-yl-propane-1,2-diol 
• 221015-49-2 (1R,2S,5S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-ol 
• 221015-46-9 (1S,5S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-one 

Downstream Products

• 131379-11-8 (E)-(4R,5S,6S,7R,8R,9R)-6,7,8,9,10-Pentakis-benzyloxy-4-methoxymethoxy-dec-2-en-5-ol 
• 119677-12-2 5,7,4'-Trimethoxy-8-<(1RS,2R,3S,4R,5R)-2,3,4,5,6-pentabenzyloxy-1-hydroxyhexyl>flavanon-ethylenacetal 
• 115678-07-4 2,3,4,5,6-penta-O-benzyl-D-glucitol 
• 121682-96-0 5-benzyloxy-1,3-dimethoxy-4-<(1RS,2R,3S,4R,5R)-1-hydroxy-2,3,4,5,6-pentabenzyloxyhexyl> benzene 
• 121682-98-2 1,3-dibenzyloxy-5-benzyloxymethyl-4-<(1RS,2R,3S,4R,5R)-1-hydroxy-2,3,4,5,6-pentabenzyloxyhexyl> benzene 
• 121682-94-8 2,3,4,5,6-penta-O-benzyl-D-gluconic acid 
• 157029-58-8 1,1-diazido-2,3,4,5,6-penta-O-benzyl-1,1-dideoxy-D-glucose 
• 50-99-7 D-glucose 
• 121709-48-6 1,3-dibenzyloxy-5-benzyloxymethyl-4-<(2R,3S,4R,5R)-2,3,4,5,6-pentabenzyloxy-1-hexanonyl> benzene 
• 121683-00-9 5-benzyloxymethyl-1,3-dimethoxy-4-<(2R,3S,4R,5R)-2,3,4,5,6-penta-benzyloxy-1-hexanonyl> benzene 
• 121682-95-9 methyl 2,3,4,5,6-penta-O-benzyl-D-gluconate 

Relevant articles and documents

Regioselective Synthesis of Difluorinated C-Furanosides Involving a Debenzylative Cycloetherification

A highly regioselective synthesis of valuable gem-difluorinated C-furanosides from unprotected aldoses via a debenzylative cycloetherification (DBCE) reaction induced by diethylaminosulfur trifluoride is descibed. The scope and limitations of this DBCE reaction are described using a series of commercially available pentoses and hexoses to afford, without selective protection/deprotection sequences, the corresponding gem-difluorinated C-furanosides in moderate to good yields.

Dapagliflozin impurity synthesis method

The invention discloses a dapagliflozin impurity synthesis method. The synthesis method includes: using D-glucose as a raw material; subjecting the D-glucose to reactions of aldehyde group protection through ethanethiol, benzyl group adding, ethanethiol removal, condensation and benzyl group removal to obtain dapagliflozin impurities. A basis is provided for study of dapagliflozin related substances.

Back to the sugars: A new enantio and diastereocontrolled route to hexoses from furfural

An integrated enantio and diastereocontrolled route to both enantiomers of the eight possible hexoses has been explored starting from furfural, by employing the Sharpless asymmetric dihydroxylation as a key step. At the present, a route to six of the eight possible hexoses has been established. The present synthesis may be taken as a reversion of the sugar-originated furfural to the sugars via a levoglucosenone, a pyrolysate of cellulose, type intermediate.