phenyl 4,6-benzylidene-2-O-(t-butyldimethylsilyl)-3-O-(2-methylnaphthyl)-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: phenyl 4,6-benzylidene-2-O-(t-butyldimethylsilyl)-3-O-(2-methylnaphthyl)-1-thio-α-D-mannopyranoside
• CAS No.: 1250346-20-3
• Molecular Formula: C₃₆H₄₂O₅SSi
• Molecular Weight: 614.878
• Mol file: 1250346-20-3.mol

Synonyms:phenyl 4,6-benzylidene-2-O-(t-butyldimethylsilyl)-3-O-(2-methylnaphthyl)-1-thio-α-D-mannopyranoside

Chemical Property of phenyl 4,6-benzylidene-2-O-(t-butyldimethylsilyl)-3-O-(2-methylnaphthyl)-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

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Technology Process of phenyl 4,6-benzylidene-2-O-(t-butyldimethylsilyl)-3-O-(2-methylnaphthyl)-1-thio-α-D-mannopyranoside

There total 1 articles about phenyl 4,6-benzylidene-2-O-(t-butyldimethylsilyl)-3-O-(2-methylnaphthyl)-1-thio-α-D-mannopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

phenyl 4,6-O-benzylidene-3-O-(2-methylnaphthyl)-1-thio-α-D-mannopyranoside (951025-06-2) + t-butyldimethylsiyl triflate (69739-34-0) → phenyl 4,6-benzylidene-2-O-(t-butyldimethylsilyl)-3-O-(2-methylnaphthyl)-1-thio-α-D-mannopyranoside (1250346-20-3)

Guidance literature:

With triethylamine; In dichloromethane; at -20 - 20 ℃; for 3h;

DOI:10.1021/ol101951u

Reference yield: 97.0%

phenyl 4,6-benzylidene-2-O-(t-butyldimethylsilyl)-3-O-(2-methylnaphthyl)-1-thio-α-D-mannopyranoside (1250346-20-3) → phenyl 4-O-benzyl-2-O-tert-butyldimethylsilyl-3-O-(naphthalene-2-ylmethyl)-1-thio-α-D-mannopyranoside

Guidance literature:

With borane-THF; di-n-butylboryl trifluoromethanesulfonate; at 0 ℃;

DOI:10.1021/acs.orglett.1c04363

Reference yield: 79.0%

phenyl 4,6-benzylidene-2-O-(t-butyldimethylsilyl)-3-O-(2-methylnaphthyl)-1-thio-α-D-mannopyranoside (1250346-20-3) + 4-methoxyphenyl [2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl]-(1→3)-[2,4-di-O-acetyl-α-L-rhamnopyranosyl]-(1→3)-2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside → 4-methoxyphenyl [2-O-tert-butyldimethylsilyl-4,6-O-benzylidene-3-O-(2-naphtyl)methyl-β-D-mannopyranosyl]-(1→3)-[2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl]-(1→3)-[2,4-di-O-acetyl-α-L-rhamnopyranosyl]-(1→3)-2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

Guidance literature:

phenyl 4,6-benzylidene-2-O-(t-butyldimethylsilyl)-3-O-(2-methylnaphthyl)-1-thio-α-D-mannopyranoside; With 1-benzenesulfinyl piperidine; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; for 1h; Molecular sieve; Inert atmosphere;

With trifluoromethylsulfonic anhydride; In dichloromethane; at -60 ℃; for 0.5h; Inert atmosphere;

4-methoxyphenyl [2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl]-(1→3)-[2,4-di-O-acetyl-α-L-rhamnopyranosyl]-(1→3)-2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside; In dichloromethane; at -60 ℃; for 1h; Inert atmosphere;

DOI:10.1055/s-0039-1690747

upstream raw materials:

phenyl 4,6-O-benzylidene-3-O-(2-methylnaphthyl)-1-thio-α-D-mannopyranoside

t-butyldimethylsiyl triflate

Downstream raw materials:

allyl 4,6-di-O-benzylidene-32-O-(t-butyldimethylsilyl)-3-O-(2-methylnaphthyl)-β-D-mannopyranosyl-(1-4)-3,6-di-O-benzyl-2-O-levulinoyl-α-D-mannopyranoside