40773-64-6

Basic information

• Product Name: .alpha.-D-ribo-Hexopyranoside, methyl 3-deoxy-4,6-O-(phenylmethylene)-
• Synonyms: .alpha.-D-ribo-Hexopyranoside, methyl 3-deoxy-4,6-O-(phenylmethylene)-;Methyl 4-O,6-O-benzylidene-3-deoxy-α-D-glucopyranoside;Methyl 4-O,6-O-benzylidene-3-deoxy-α-D-ribo-hexopyranoside
• CAS NO: 40773-64-6
• Molecular Formula: C₁₄H₁₈O₅
• Molecular Weight: 266.28972
• Mol File: 40773-64-6.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: .alpha.-D-ribo-Hexopyranoside, methyl 3-deoxy-4,6-O-(phenylmethylene)-(CAS DataBase Reference)
• NIST Chemistry Reference: .alpha.-D-ribo-Hexopyranoside, methyl 3-deoxy-4,6-O-(phenylmethylene)-(40773-64-6)
• EPA Substance Registry System: .alpha.-D-ribo-Hexopyranoside, methyl 3-deoxy-4,6-O-(phenylmethylene)-(40773-64-6)

Safety Data

• Hazardous Substances Data: 40773-64-6(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 24332-89-6 methyl-(α-D-lyxo-3-deoxy-hexopyranoside) 
• 2880-96-8 methyl 2,3-anhydro-4,6-dioxabenzylidene-α-D-talopyranose 
• 16697-40-8 methyl-[O⁴,O⁶-((S)-benzylidene)-S-methyl-3-thio-β-D-idopyranoside] 
• 2280-44-6 D-Glucose 
• 34266-73-4 methyl 4,6-O-benzylidene-3-deoxy-α-D-arabino-hexopyranoside 
• 6748-86-3 methyl 4,6-O-benzylidene-2,3-di-O-p-tolylsulfonyl-α-D-mannopyranoside 
• 688-73-3 tri-n-butyl-tin hydride 
• 2880-96-8 (1aR,2S,6R,7aR,7bR)-2-Methoxy-6-phenyl-hexahydro-1,3,5,7-tetraoxa-cyclopropa[a]naphthalene 
• 4234-42-8 methyl 4,6-O-benzylidene-2-O-p-toluenesulphonyl-α-D-ribohexopyranosid-3-ulose 
• 6698-32-4 methyl 4,6-O-benzylidene-2-O-toluene-p-sulfonyl-α-D-glucopyranoside 
• 3150-16-1 methyl 4,6-O-benzylidene-2,3-anhydro-α-D-mannopyranoside 
• 6748-86-3 methyl 4,6-O-benzylidene-3-O-p-tolylsulfonyl-α-D-allopyranoside 
• 28538-12-7 methyl 2-O-benzoyl-4,6-O-benzylidene-3-O-p-tolylsulfonyl-α-D-allopyranoside 

Downstream Products

• 145149-83-3 Methyl 2,4-di-O-benzyl-3-deoxy-α-D-ribo-hexopyranoside 
• 152838-14-7 (2R,4S)-dibenzyloxy-1,1-dimethoxy-hex-5-ene 
• 152838-13-6 (2R,4S)-dibenzyloxyhex-5-enal 
• 152838-12-5 methyl 2,4-di-O-benzyl-3,6-dideoxy-6-iodo-α-D-ribo-hexopyranoside 
• 152838-16-9 (2R,4R)-dibenzyloxy-6-tert-butyldiphenylsilyloxy-hexanal 
• 152838-15-8 (2R,4R)-dibenzyloxy-6-tert-butyldiphenylsilyloxy-1,1-dimethoxy-hexane 
• 152838-17-0 methyl (2R,4R)-dibenzyloxy-6-tert-butyldiphenylsilyloxy-hexanoate 
• 152838-18-1 dimethyl <(3R,5R)-dibenzyloxy-7-tert-butyldiphenylsilyloxy-heptan-2-on-1-yl> phosphonate 
• 99613-17-9 (2S,4R,5R)-4,6-Bis-benzyloxy-2-benzyloxycarbonylamino-5-hydroxy-hexanoic acid methyl ester 
• 99613-18-0 (2S,4R,5S)-4,6-Bis-benzyloxy-2-benzyloxycarbonylamino-5-chloro-hexanoic acid methyl ester 
• 99613-16-8 ((3S,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-oxo-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester 
• 99613-15-7 ((2S,3S,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester 

Relevant articles and documents

Site-selective catalysis of phenyl thionoformate transfer as a tool for regioselective deoxygenation of polyols

(Chemical Equation Presented) We report the application of peptide-embedded imidazoles as catalysts for the site-selective delivery of the phenyl thionoformate unit as a prelude to deoxygenation reactions of polyols. Methodology was developed that allows for the synthesis of thiocarbonyl derivatives based on a combination of additives that include N-alkylimidazoles and FeCl3 as co-catalysts. The use of this reagent combination leads to increased reaction rates and efficient yields relative to those of simple base-mediated reactions. In terms of controlling regioselectivity during the course of polyol modification, we found that histidine-containing peptides, in combination with FeCl3, could lead to modulation of the product distribution. Through screening of peptides and control of reaction conditions, products could be observed that reflected both the inherent preference of substrates and also reversal of inherent selectivity.

An Efficient Deoxysugar Synthesis using Bu4NBH4 via an SN2 Reduction

Deoxysugar derivatives were prepared from the corresponding triflate, tosylate, halogen, and epoxide derivatives.Employing the tetrabutylammonium tetrahydroborate reagent, the deoxygenation proceeds via an SN2 type displacement in good yield.

Free radical mediated reduction and deoxygenation of epoxides

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