35813-17-3

Basic information

• Product Name: 3-O,4-O,5-O,6-O-Tetraacetyl-2-deoxy-D-arabino-hexonic acid methyl ester
• Synonyms: 3-O,4-O,5-O,6-O-Tetraacetyl-2-deoxy-D-arabino-hexonic acid methyl ester
• CAS NO: 35813-17-3
• Molecular Weight: 0
• Mol File: 35813-17-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-O,4-O,5-O,6-O-Tetraacetyl-2-deoxy-D-arabino-hexonic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O,4-O,5-O,6-O-Tetraacetyl-2-deoxy-D-arabino-hexonic acid methyl ester(35813-17-3)
• EPA Substance Registry System: 3-O,4-O,5-O,6-O-Tetraacetyl-2-deoxy-D-arabino-hexonic acid methyl ester(35813-17-3)

Safety Data

• Hazardous Substances Data: 35813-17-3(Hazardous Substances Data)

Upstream product

• 35926-82-0 (3R,4S,5R)-3,4,5,6-Tetraacetoxy-2-diazo-hexanoic acid methyl ester 
• 42015-03-2 Methyl-(3,4,6-tri-O-acetyl-2-desoxy-gluconat) 
• 108-24-7 acetic anhydride 
• 27963-68-4 2-Desoxy-D-arabino-hexonsaeuremethylester 
• 35813-12-8 Methyl-2-amino-2-desoxy-D-gluconat-hydrochlorid 
• 2873-29-2 D-glucal triacetate 

Downstream Products

• 7241-20-5 (2R,3S,4R)-pentane-1,2,3,4-tetrayl tetraacetate 

Relevant articles and documents

ABRAMOW-REAKTION VON KOHLENHYDRATDERIVATEN MIT FREIEN ANOMEREN ZENTREN

Diisopropylidene mannofuranose (1) and dimethylphosphite react under base catalysis in an Abramow reaction with subsequent internal transesterification to yield the diasteromeric δ-phostones 2, which are also transformed into their crystalline tosylates 3.Surprisingly these compounds adapt a boat conformation, however, after change of the protecting groups a flat chair conformation (of 8 and 9) results.The δ-phostone formation (7) turned out to be the preferred reaction course even when the cyclic phosphite 6 is applied to react with 1.In basic medium the tosylate 3 does not undergo a ring contraction to a glycosyl phosphonate, however the 2-desoxy mannonic acid ester 10 is obtained: this is discussed and a mechanism proposed.Starting with the ribofuranose derivative 12 the corresponding δ-phostones 14 are prepared.In the reaction of the glucopyranose compound 16 a competition between the formation of ε-phostones 19 and the open-chain phosphonates 21 is observed.

Diazo Derivatives of Sugars. Synthesis of methyl 2-deoxy-2-Diazo-d-arabino-Hexonate, Its Behaviour on Photolysis and Thermolysis, and Conversion into a Pyrazole Derivative

The action of nitrous acid on methyl 2-amino-2-deoxy-d-gluconate hydrochloride (5) and acetylation of the product gives methyl 3,4,5,6-tetra-O-acetyl-2deoxy-2-diazo-d-arabino-hexonate (6); 4,6-O-benzylidene analogs of the methyl (4) and ethyl (3) esters are similarly prepared. Photolysis of the diazo sugar 6 in isopropyl alcohol gives mainly methyl 3,4,5,6-tetra-O-acetyl-2-deoxy-d-arabino-hexonate (13) and a small proportion of methyl 4,5,6-tri-O-acetyl-2,3-dideoxy-trans,-d-erythro-hex2-enoate (14), whereas photolysis of 6 in methanol gave a cis,trans mixture of methyl 3,4,5,6-tetra-O-acetyl-2-deoxy-d-erythro-hex-2-enoate (10); the same mixture (10) of enol acetates was obtained by thermolysis of 6. The diazo sugar 6 underwent cycloaddition with phenylacetylene to give a crystalline (R or S)-3-(d-arabino-tetraacetoxybutyl)-3-methoxycarbonyl-5-phenyl-3H-pyrazole (9) in 85% yield.