78342-32-2

Basic information

• Product Name: Methyl 4,6-O-benzylidene-3-O-(t-butyldimethylsilyl)-α-D-ribo-hexopyranosid-2-uloside
• Synonyms: Methyl 4,6-O-benzylidene-3-O-(t-butyldimethylsilyl)-α-D-ribo-hexopyranosid-2-uloside
• CAS NO: 78342-32-2
• Molecular Weight: 394.54
• Mol File: 78342-32-2.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Methyl 4,6-O-benzylidene-3-O-(t-butyldimethylsilyl)-α-D-ribo-hexopyranosid-2-uloside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 4,6-O-benzylidene-3-O-(t-butyldimethylsilyl)-α-D-ribo-hexopyranosid-2-uloside(78342-32-2)
• EPA Substance Registry System: Methyl 4,6-O-benzylidene-3-O-(t-butyldimethylsilyl)-α-D-ribo-hexopyranosid-2-uloside(78342-32-2)

Safety Data

• Hazardous Substances Data: 78342-32-2(Hazardous Substances Data)

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 112711-35-0 methyl 3-O-[(1,1-dimethylethyl)dimethylsilyl]-4,6-O-[(R)-phenylmethylene]-α-D-glucopyranoside 

Downstream Products

• 78329-24-5 Methyl 4,6-O-Benzylidene-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-C-(formylmethyl)-2-C-vinyl-α-D-glucopyranoside 
• 78329-23-4 Methyl 4,6-O-Benzylidene-2-deoxy-2-C-(((vinyloxy)methyl)methylene)-α-D-arabino-hexopyranoside 
• 78342-33-3 Methyl 4,6-O-Benzylidene-2-deoxy-2-C-(formylmethyl)-2-C-vinyl-α-D-glucopyranoside lactol 
• 78342-35-5 Methyl 4,6-O-Benzylidene-2,3-dideoxy-2-C-(2-methoxyethyl)-2-C-vinyl-α-D-ribo-hexopyranoside 
• 89872-86-6 Methyl 4,6-O-Benzylidene-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-C-(((vinyloxy)methyl)methylene)-α-D-arabino-hexopyranoside 
• 89889-10-1 Methyl 4,6-O-Benzylidene-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-C-((hydroxymethyl)methylene)-α-D-arabino-hexopyranoside 
• 89872-85-5 Methyl 4,6-O-Benzylidene-2-deoxy-2-C-((hydroxymethyl)methylene)-α-D-arabino-hexopyranoside acetonide 
• 89872-84-4 (2R,4aR,6S,8R,8aS)-7-[2-Hydroxy-eth-(E)-ylidene]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol 
• 136904-68-2 -2-spiro-5'-(4'-amino-1',2'-oxathiole-2',2'-dioxide) 
• 136919-89-6 methyl 4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-2-C-cyano-2-O-mesyl-α-D-glucopyranoside 
• 193149-53-0 tert-Butyl-{(2R,4aR,6S,8R,8aR)-7-[1-fluoro-meth-(E)-ylidene]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-dimethyl-silane 
• 193149-55-2 (2R,4aR,6S,8aS)-6-Methoxy-2-phenyl-7-trifluoromethyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine 
• 193149-51-8 tert-Butyl-((2R,4aR,6S,8R,8aR)-7-difluoromethylene-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-dimethyl-silane 
• 78329-22-3 Methyl 4,6-O-Benzylidene-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-C-((E)-carbethoxymethylene)-α-D-arabino-hexopyranoside 

Relevant articles and documents

Highly Stereoselective Introduction of Fluorine-Containing Methyl Groups at 2 Position of D-Glucose

Highly stereoselective introduction of fluorine-containing methyl groups at the 2 position of methyl glucoside was attained by use of the difluoromethylene derivative as a key intermediate via hydrogenation of exo- and endo-olefins, whose diastereofacial selectivity was considered to be governed by the anomeric methoxy group.

The 'Off-template' Problem: Towards a General Solution

Wittig reaction of the t-butyldimethylsilylated C-3 ketone methyl 4,6-O-benzylidene-2-O-(t-butyldimethylsilyl)-α-D-ribo-hexopyranosid-3-uloside leads exclusively to C-2 alkenes, providing an efficient synthesis of these potentially useful intermediates.Alternatively, the corresponding t-butyldiphenylsilyl ether, prepared with complete regiospecificity from methyl 4,6-O-benzylidene-α-D-glucopyranoside, gives a C-3 alkene on oxidation and Wittig reaction.Deprotection, hydrogenation and cyclization of this product leads to the cis-fused butyrolactone, methyl 4,6-O-benzylidene-3-deoxy-3-(ethoxycarbonyl)-2,3-butyrolactone-α-D-allopyranoside, which is alkylated stereospecifically to give methyl 4,6-O-benzylidene-3-deoxy-3-(prop-2-yloxycarbonyl)-2,3-butyrolacto-α-D-allopyranoside.This procedure provides a general solution of the 'off-template' problem of carbohydrate-based natural product synthesis.

Out-of-Ring Claisen Rearrangement are Highly Stereoselective in Pyranoses: Routes to gem-Dialkylated Sugars

The Claisen rearrangement has been evaluated as a means for stereoselective creation of functionalized geminal substituents at C-2 and C-3 of hexopyrano systems.C-2 and C-3 keto sugars react with Wittig reagents to give α,β-unsaturated esters, one geometric isomer being obtained in each case.Reduction of the ester and trans vinylation with ethyl vinyl ether leads to allyl vinyl ethers wich are thermolysed in refluxing benzonitrile.The oxy-Cope rearrengement proceeds with complete stereoselectivity, the folding pattern being always from the β-face of the pyranose ring.Thus, the acetaldehyde moiety ends up axially oriented at C-2 and equatorially oriented at C-3.These stereochemical results are not affected by neighboring oxygen substituents nor by the presence or absence of an anomeric alkoxyl functionality.