136656-50-3

Basic information

• Product Name: (2R,3R,4R)-((3,4-bis(benzyloxy)-3,4-dihydro-2H-pyran-2-yl)-methoxy)(tert-butyl)dimethylsilane
• Synonyms: (2R,3R,4R)-((3,4-bis(benzyloxy)-3,4-dihydro-2H-pyran-2-yl)-methoxy)(tert-butyl)dimethylsilane
• CAS NO: 136656-50-3
• Molecular Weight: 440.655
• Mol File: 136656-50-3.mol

Chemical Properties

• CAS DataBase Reference: (2R,3R,4R)-((3,4-bis(benzyloxy)-3,4-dihydro-2H-pyran-2-yl)-methoxy)(tert-butyl)dimethylsilane(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4R)-((3,4-bis(benzyloxy)-3,4-dihydro-2H-pyran-2-yl)-methoxy)(tert-butyl)dimethylsilane(136656-50-3)
• EPA Substance Registry System: (2R,3R,4R)-((3,4-bis(benzyloxy)-3,4-dihydro-2H-pyran-2-yl)-methoxy)(tert-butyl)dimethylsilane(136656-50-3)

Safety Data

• Hazardous Substances Data: 136656-50-3(Hazardous Substances Data)

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 4098-06-0 triacetyl-D-galactal 
• 21193-75-9 D-galactal 
• 124751-19-5 (2R,3R,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol 
• 100-39-0 benzyl bromide 

Downstream Products

• 1202398-23-9 C₅₉H₆₆N₂O₁₆Si 
• 130257-64-6 methyl 4-O-(2-azido-6-O-benzoyl-3,4-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranoside 
• 130278-33-0 methyl 4-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-sulfo-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranosiduronic acid, disodium salt 
• 130278-32-9 methyl uronate 
• 130257-66-8 methyl uronate 

Relevant articles and documents

Synthesis and biological evaluation of α-galactosylceramide analogues with heteroaromatic rings and varying positions of a phenyl group in the sphingosine backbone

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Treatment of 5-vinylpyranosides with Et2Zn and catalytic Pd(0), in the presence of ZnCl2, results in the formation of 5-membered carbocyclic products. This carbohydrate ring-contraction features an intramolecular allylation of a ring-opened carbohydrate aldehyde by an in situ-generated nucleophilic allylzinc species. The stereoselectivity about vinyl and free hydroxyl groups at the newly created stereogenic centers varies from low to moderate while both its extent and sense are found to depend on particular structural features (e.g. the configuration of the starting carbohydrate).

Substituent effects on the SmI2/Pd(0)-promoted carbohydrate ring-contraction of 5-alkynylpyranosides

The effect of substituents on the reactivity and stereoselectivity of the SmI2/Pd(0)-promoted ring-contraction of 5-alkynylpyranosides has been examined using substrates substituted only at selected positions. While formation of 2-ethynylcyclopentanols takes place efficiently, an internal alkyne did not afford the expected product. The presence of peripheral alkoxy substituents leads to variable stereoselectivities that depend on the number and orientation of such groups. Thus, an isolated OBn substituent at C(3) (carbohydrate numbering) exerts a significant stereochemical control while additional substitution with the same group at C(4) either enhances or drastically reduces stereoselectivity depending on its orientation (α or β, respectively).

A New General Route to the Synthesis of Bicyclic Synthons from Glycals

Iodonium sym-dicollidine perchlorate (IDCP: bis(2,4,6-trimethylpyridine)iodine(1+) perchlorate) mediated intramolecular iodoalkoxylation of 3,4-di-O-substituted glycals 9a-14f gives rise to synthetically useful chiral bicyclic synthons 15a-20f respectivel

Syntheses of the methyl glycosides of the repeating units of chondroitin 4- and 6-sulfate.

3,4,6-Tri-O-acetyl-D-galactal was transformed into methyl 6-O-acetyl-2-azido-4-O-benzyl-2-deoxy-beta-D-galactopyranoside and its 4-O-acetyl-6-O-benzyl analogue, each of which was glycosylated with activated, O-acetylated derivatives of methyl D-glucopyranosyluronate. The resulting beta-(1----3)-linked disaccharide derivatives were each reductively N-acetylated, hydrogenolysed, O-sulfated, and saponified to afford the disodium salts of methyl 2-acetamido-2-deoxy-3-O-(beta-D-glucopyranosyluronic acid)-4-O-sulfo-beta-D-galactopyranoside and the 6-O-sulfo analogue. D-Galactal was also transformed into activated derivatives of 2-azido-3,6-di-O-benzyl-2-deoxy-D-galactopyranose and their 3,4-di-O-benzyl analogues with various substituents at O-4 and O-6. These glycosyl donors were condensed with 6-O-protected derivatives of methyl 2,3-di-O-benzyl-beta-D-glucopyranoside to give the beta-(1----4)-linked disaccharide derivatives, which were selectively deprotected, then oxidised at C-6 of the gluco unit, reductively N-acetylated, selectively deprotected, O-sulfated at C-4 or C-6 of the galacto unit, and hydrogenolysed to give the disodium salts of methyl 4-O-(2-acetamido-2-deoxy-4-O-sulfo-beta-D-galactopyranosyl)-beta-D- glucopyranosiduronic acid and the 6-O-sulfo analogue.