methyl 2,3,6-tri-O-benzyl-4-O-[4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-tert-butyldimethylsilyl-β-D-mannopyranosyl]-(1->4)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2,3,6-tri-O-benzyl-4-O-[4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-tert-butyldimethylsilyl-β-D-mannopyranosyl]-(1->4)-α-D-glucopyranoside
• CAS No.: 855306-41-1
• Molecular Formula: C₅₀H₆₂O₁₁Si
• Molecular Weight: 867.121
• Mol file: 855306-41-1.mol

Synonyms:methyl 2,3,6-tri-O-benzyl-4-O-[4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-tert-butyldimethylsilyl-β-D-mannopyranosyl]-(1->4)-α-D-glucopyranoside

Chemical Property of methyl 2,3,6-tri-O-benzyl-4-O-[4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-tert-butyldimethylsilyl-β-D-mannopyranosyl]-(1->4)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3,6-tri-O-benzyl-4-O-[4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-tert-butyldimethylsilyl-β-D-mannopyranosyl]-(1->4)-α-D-glucopyranoside

There total 4 articles about methyl 2,3,6-tri-O-benzyl-4-O-[4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-tert-butyldimethylsilyl-β-D-mannopyranosyl]-(1->4)-α-D-glucopyranoside 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:

phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(tert-butyldimethylsilyl)-1-thio-α-D-mannopyranoside (855306-34-2) + methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) → methyl 2,3,6-tri-O-benzyl-4-O-[4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-tert-butyldimethylsilyl-β-D-mannopyranosyl]-(1->4)-α-D-glucopyranoside (855306-41-1) + methyl 2,3,6-tri-O-benzyl-4-O-[4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-tert-butyldimethylsilyl-α-D-mannopyranosyl]-(1->4)-α-D-glucopyranoside

Guidance literature:

phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(tert-butyldimethylsilyl)-1-thio-α-D-mannopyranoside; With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; 4 A molecular sieve; In dichloromethane; at -60 ℃; for 0.5h;

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside; In dichloromethane; at -60 ℃; for 2h;

DOI:10.1021/ol050680g

Reference yield:

phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-1-thio-α-D-mannopyranoside (855306-33-1) → methyl 2,3,6-tri-O-benzyl-4-O-[4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-tert-butyldimethylsilyl-β-D-mannopyranosyl]-(1->4)-α-D-glucopyranoside (855306-41-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 92 percent / imidazole / dimethylformamide / 12 h / 20 °C

2.1: 1-benzenesulfinyl piperidine; 2,4,6-tri-tert-butylpyrimidine; trifluoromethanesulfonic anhydride / CH₂Cl₂ / 0.5 h / -60 °C

2.2: CH₂Cl₂ / 2 h / -60 °C

With 1H-imidazole; 1-benzenesulfinyl piperidine; trifluoromethanesulfonic acid anhydride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo0526789

Reference yield:

phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside (855306-32-0) → methyl 2,3,6-tri-O-benzyl-4-O-[4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-tert-butyldimethylsilyl-β-D-mannopyranosyl]-(1->4)-α-D-glucopyranoside (855306-41-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 93 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 20 °C

2.1: 92 percent / imidazole / dimethylformamide / 12 h / 20 °C

3.1: 1-benzenesulfinyl piperidine; 2,4,6-tri-tert-butylpyrimidine; trifluoromethanesulfonic anhydride / CH₂Cl₂ / 0.5 h / -60 °C

3.2: CH₂Cl₂ / 2 h / -60 °C

With 1H-imidazole; 1-benzenesulfinyl piperidine; trifluoromethanesulfonic acid anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo0526789

upstream raw materials:

phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(tert-butyldimethylsilyl)-1-thio-α-D-mannopyranoside

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-1-thio-α-D-mannopyranoside

phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside