114861-44-8

Basic information

• Product Name: Benzoic acid (2R,3S,4R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3,4-dihydro-2H-pyran-4-yl ester
• Synonyms: Benzoic acid (2R,3S,4R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3,4-dihydro-2H-pyran-4-yl ester
• CAS NO: 114861-44-8
• Molecular Weight: 364.514
• Mol File: 114861-44-8.mol

Chemical Properties

• CAS DataBase Reference: Benzoic acid (2R,3S,4R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3,4-dihydro-2H-pyran-4-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid (2R,3S,4R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3,4-dihydro-2H-pyran-4-yl ester(114861-44-8)
• EPA Substance Registry System: Benzoic acid (2R,3S,4R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3,4-dihydro-2H-pyran-4-yl ester(114861-44-8)

Safety Data

• Hazardous Substances Data: 114861-44-8(Hazardous Substances Data)

Upstream product

• 58871-09-3 6-O-tert-butyldimethylsilyl-D-glucal 
• 98-88-4 benzoyl chloride 
• 2873-29-2 D-glucal triacetate 
• 13265-84-4 D-glucal 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 114861-45-9 (-)-(2S,4S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(benzoyloxy)-3,4-dihydro-2H-pyran 
• 114861-47-1 (-)-(2S,4S)-2-(hydroxymethyl)-4-(benzyloxy)-3,4-dihydro-2H-pyran 
• 114861-48-2 (-)-(2S,4S)-4-(benzyloxy)-3,4-dihydro-2H-pyran-2-carboxaldehyde 
• 114861-46-0 (-)-(2S,4S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(benzyloxy)-3,4-dihydro-2H-pyran 
• 114861-57-3 Benzoic acid (2R,3S,4R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-methylsulfanylthiocarboxyoxy-3,4-dihydro-2H-pyran-4-yl ester 
• 1152164-71-0 C₁₉H₂₉NO₇SSi 
• 137792-71-3 [(1S,3S,4S,6R,7S,8R)-7-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-8-methoxymethoxy-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester 
• 137792-71-3 [(1S,3S,4S,6S,7S,8R)-7-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-8-methoxymethoxy-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester 
• 137822-71-0 ((1R,3S,4S,5R,6S,7S,8R)-7-Benzyloxy-6-hydroxy-3-methoxy-8-methoxymethoxy-2-oxa-bicyclo[2.2.2]oct-5-yl)-acetic acid ethyl ester 
• 137894-31-6 ((1R,3S,4S,5S,6R,7S,8R)-7-Benzyloxy-6-hydroxy-3-methoxy-8-methoxymethoxy-2-oxa-bicyclo[2.2.2]oct-5-yl)-acetic acid ethyl ester 
• 137792-72-4 (1R,2R,6R,7S,8S,10S,11R)-10-Benzyloxy-8-methoxy-11-methoxymethoxy-3,9-dioxa-tricyclo[5.2.2.0^2,6]undecan-4-one 
• 137792-72-4 (1R,2S,6S,7S,8S,10S,11R)-10-Benzyloxy-8-methoxy-11-methoxymethoxy-3,9-dioxa-tricyclo[5.2.2.0^2,6]undecan-4-one 
• 137792-76-8 Ethyl 3,5-Diacetoxy-6-(benzoyloxy)-4-(benzyloxy)-2-<2-(1,3-dithianyl)>cyclohex-1-ylacetate 
• 137792-93-9 Benzoic acid (1R,3S,4S,5R,6S,7S,8R)-7-benzyloxy-5-ethoxycarbonylmethyl-3-methoxy-8-methoxymethoxy-2-oxa-bicyclo[2.2.2]oct-6-yl ester 

Relevant articles and documents

Radical Cyclization Routes to Bridged Pyranosides as Precursors of Densely Functionalized Cycloalkanes

Glycals derived from hexapyranoses permit the incorporation of iodine at C-2 as well as elaboration of an olefinic residue via the C-5-hydroxymethyl group.Radical cyclization of these functionalities leads to bicyclic systems whose bridge sizes depend on

Synthesis of a Structurally Modified Glycal. (-)-(2R,4S)-2-Methyl-2-vinyl-4-(benzyloxy)-3,4-dihydro-2H-pyran

A synthetic procedure for the transformation of levoglucosan (4) to (-)-(2R,4S)-2-methyl-2-vinyl-4-(benzyloxy)-3,4-dihydro-2H-pyran (1) in 11 steps is described.The scheme relies on selective deoxygenation of the pair of α-hydroxyl groups, blocking of the β-hydroxyl, and formation of ester 16.The presence of the carboxylate group allows for stereocontrolled methylation of the enolate anion, conversion of ester to vinyl, and ultimate eliminative removal of the methoxyl substituent in methyl glycoside 25.This key transformation takes advantage of regioselective acetal cleavage by trimethylsilyl iodide and in situ dehydroiodination of the product so formed with hexamethyldisilazane.Certain unsuccessful attempts to form the α-lithio anion of 1 are also discussed.