196703-96-5

Upstream product

• 13154-24-0 triisopropylsilyl chloride 
• 21193-75-9 D-galactal 
• 4098-06-0 triacetyl-D-galactal 
• 100-39-0 benzyl bromide 
• 166021-01-8 1,5-anhydro-6-O-triisopropylsilyl-2-deoxy-D-lyxo-hex-1-enitol 

Downstream Products

• 196703-99-8 thioethyl 3,4-di-O-benzyl-6-O-triisopropylsilyl-β-D-galactopyranoside 
• 196704-06-0 Acetic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-2-ethylsulfanyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester 
• 196704-13-9 thioethyl 3,4-di-O-benzyl-2-O-pivaloyl-6-O-triisopropylsilyl-β-D-galactopyranoside 
• 196704-09-3 Benzoic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-2-ethylsulfanyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester 
• 196704-60-6 3,4-di-O-benzyl-2-O-pivaloyl-6-O-triisopropylsilyl-β-D-galactopyranoside-(1->4)-3,6-di-O-benzyl-D-glucal 
• 196705-02-9 thioethyl 3,4-di-O-benzyl-2-O-pivaloyl-6-O-triisopropylsilyl-β-D-galactopyranoside-(1->4)-3,6-di-O-benzyl-β-D-glucopyranoside 
• 196705-03-0 thioethyl 3,4-di-O-benzyl-2-O-pivaloyl-6-O-triisopropylsilyl-β-D-galactopyranoside-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside 
• 196705-04-1 3,4-di-O-benzyl-2-O-pivaloyl-6-O-triisopropylsilyl-β-D-galactopyranoside-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside-(1->4)-3,6-di-O-benzyl-D-glucal 
• 130323-37-4 (2R,3R,4R)-(3,4-bis(benzyloxy)-3,4-dihydro-2H-pyran-2-yl)methanol 

Relevant academic research and scientific papers

Stereoselective glycosylation of 2-nitrogalactals catalyzed by a bifunctional organocatalyst

The use of a bifunctional cinchona/thiourea organocatalyst for the direct and α-stereoselective glycosylation of 2-nitrogalactals is demonstrated for the first time. The conditions are mild, practical, and applicable to a wide range of glycoside acceptors with products being isolated in good to excellent yields. The method is exemplified in the synthesis of mucin type Core 6 and 7 glycopeptides.

α-Selective organocatalytic synthesis of 2-deoxygalactosides

Alpha rules: A thiourea acts as an efficient organocatalyst for the glycosylation of protected galactals to form oligosaccharides containing a 2-deoxymonosaccharide moiety (see scheme). The reaction is highly stereoselective for α-linkages and proceeds by way of a syn-addition mechanism. Copyright

Immunomodulating glycosphingolipids: An efficient synthesis of a 2′-deoxy-α-galactosyl-GSL

A new and efficient approach to the total synthesis of 2′-deoxy-α-galactosyl glycosphingolipids was accomplished. Commercially available 3,4,6-tri-O-acetylgalactal was used as the chiral starting material for both the sugar and phytosphingosine building blocks required for the synthesis of 1-O-(2-deoxy-α-D-galactopyranosyl)-2-docosanoylamino-1,3, 4-octadecanetriol. The key step of the synthetic strategy was the stereoselective α-glycosidation of the azido precursor of sphingosine.