1072523-01-3

Basic information

• Product Name: 3-(2',3'-di-O-benzyl-4',6'-O-benzylidene-α-D-glucopyranosyl)-1-propene
• Synonyms: 3-(2',3'-di-O-benzyl-4',6'-O-benzylidene-α-D-glucopyranosyl)-1-propene
• CAS NO: 1072523-01-3
• Molecular Weight: 472.581
• Mol File: 1072523-01-3.mol

Chemical Properties

• CAS DataBase Reference: 3-(2',3'-di-O-benzyl-4',6'-O-benzylidene-α-D-glucopyranosyl)-1-propene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2',3'-di-O-benzyl-4',6'-O-benzylidene-α-D-glucopyranosyl)-1-propene(1072523-01-3)
• EPA Substance Registry System: 3-(2',3'-di-O-benzyl-4',6'-O-benzylidene-α-D-glucopyranosyl)-1-propene(1072523-01-3)

Safety Data

• Hazardous Substances Data: 1072523-01-3(Hazardous Substances Data)

Upstream product

• 915285-80-2 trifluoromethanesulfonyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 24850-33-7 allyltributylstanane 
• 762-72-1 allyl-trimethyl-silane 
• 219586-38-6 phenylsulfenyl 3-(2',3'-di-O-benzyl-4',6'-O-benzylidene)-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 181267-07-2 (2R,4aR,6R,7R,8R,8aS)-6-Allyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 87470-70-0 S-phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 103773-87-1 (2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranosyl)-prop-2-ene 

Relevant articles and documents

Mild cu(Otf)2-mediated C-glycosylation with chelation-assisted picolinate as a leaving group

C-Glycosylation reactions of glycosyl picolinates with allyltrimethylsilane or silyl enol ethers were developed. Picolinate as a chelation-assisted leaving group could be activated by Cu(OTf)2 and avoided the use of harsh Lewis acids. The glycosylations were operated under mild neutral conditions and gave the corresponding C-glycosides in up to 95% yield with moderate to excellent stereoselectivities.

Synthesis of Conformationally-Locked cis- and trans-Bicyclo[4.4.0] Mono-, Di-, and Trioxadecane Modifications of Galacto- and Glucopyranose; Experimental Limiting 3JH,H Coupling Constants for the Estimation of Carbohydrate Side Chain Populations and beyond

Hexopyranose side chains populate three staggered conformations, whose proportions can be determined from the three sets of ideal limiting 3JH5,H6R and 3JH5,H6S coupling constants in combination with the time-averaged experimental coupling constants. Literature values for the limiting coupling constants, obtained by the study of model compounds, the use of the Haasnoot-Altona and related equations, or quantum mechanical computations, can result in computed negative populations of one of the three ideal conformations. Such values arise from errors in the limiting coupling constants and/or from the population of nonideal conformers. We describe the synthesis and analysis of a series of cis- and trans-fused mono-, di-, and trioxabicyclo[4.4.0]octane-like compounds. Correction factors for the application of data from internal models (-CH(OR)-CH(OR)-) to terminal systems (-CH(OR)-CH2(OR)) are deduced from comparison of further models, and applied where necessary. Limiting coupling constants so-derived are applied to the side chain conformations of three model hexopyranosides, resulting in calculated conformer populations without negative values. Although, developed primarily for hexopyranose side chains, the limiting coupling constants are suitable, with the correction factors presented, for application to the side chains of higher carbon sugars and to conformation analysis of acyclic diols and their derivatives in a more general sense.

Stereoselective C -glycoside formation with 2- O -benzyl-4,6- O -benzylidene protected 3-deoxy gluco- and mannopyranoside donors: Comparison with o -glycoside formation

Unlike alcohols, the reaction of C-nucleophiles with 2-O-benzyl-4,6-O- benzylidene-protected 3-deoxy-gluco- and mannopyranosyl thioglycosides is highly stereoselective providing the α-C-glycosides in the gluco-series and the β-C-glycosides in the manno-series. Conformational analysis of nucleophilic attack of putative intermediate glycosyl oxocarbenium ions suggests that the observed selectivities for C-glycoside formation can be explained by preferential attack on the opposite face of the oxocarbenium to the C2-H2 bond and that eclipsing interactions with this bond are the main stereodetermining factor. It is argued that the steric interactions in the attack of alcohols (sp3-hybridized O) and of typical carbon-based nucleophiles (sp 2 C) on oxocarbenium ions are very different, with the former being less severe, and thus that there is no a priori reason to expect O- and C-glycosylation to exhibit parallel stereoselectivities for attack on a given oxocarbenium ion.

Is donor-acceptor hydrogen bonding necessary for 4,6-O-benzylidene-directed β-mannopyranosylation? stereoselective synthesis of β-C- mannopyranosides and α-C-glucopyranosides

(Equation Presented) 2,3-Di-O-benzyl-4,6-0-benzylidene-thiohexopyranosides: on activation with 1-benzenesulfinyl piperidine and triflic anhydride, react with allyl silanes and stannanes, and with silyl enolethers to give C-glycosides. In the mannose serie

Studies on the stereoselective synthesis of C-allyl glycosides

(Equation Presented) An investigation was carried out to explore the use of sulfoxide donors as common precursors to stereoisomeric C-glycoconjugates of glycoprotein and glycolipid tumor antigens. A study focusing on the effects of reaction conditions and substrate structure on the stereoselectivity of allylation was carried out. Although conditions were realized to selectively afford α-allylation products in good to excellent yields, the search for conditions favoring β-selectivity proved less successful.