tert-butyldimethylsilyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

Base Information

Chemical Name:tert-butyldimethylsilyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside
CAS No.:637763-50-9
Molecular Formula:C₅₀H₆₀Cl₃NO₁₂Si
Molecular Weight:1001.47
Hs Code.:

tert-butyldimethylsilyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

Synonyms:tert-butyldimethylsilyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

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Chemical Property of tert-butyldimethylsilyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

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Technology Process of tert-butyldimethylsilyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

There total 5 articles about tert-butyldimethylsilyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-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:

: 108-24-7
acetic anhydride

: 637763-66-7
N-[(2S,3R,4R,5S,6R)-4-Benzyloxy-5-((2R,4aR,6S,7S,8S,8aS)-7-benzyloxy-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-3-yl]-2,2,2-trichloro-acetamide

: 637763-50-9
tert-butyldimethylsilyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

Guidance literature:: With dmap; In dichloromethane; at 0 - 20 ℃; for 2.08333h;
DOI:10.1021/ol035887t

Reference yield:

: phenyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside S-oxide

: 637763-50-9
tert-butyldimethylsilyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 68 percent / di(tert-butyl)pyridine; triflic anhydride / CH₂Cl₂ / 1.25 h / -78 °C

2: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; water / CH₂Cl₂ / 0.75 h

3: 771 mg / 4-(dimethylamino)pyridine / CH₂Cl₂ / 2.08 h / 0 - 20 °C

With dmap; trifluoromethylsulfonic anhydride; di(tert-butyl)pyridine; water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane;
DOI:10.1021/ol035887t

Reference yield:

: N-[(2R,4aR,6S,7R,8R,8aS)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-2,2,2-trichloro-acetamide

: 637763-50-9
tert-butyldimethylsilyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 63 percent / triethylsilane; trifluoromethanesulfonic acid; trifluoromethanesulfonic acid anhydride / CH₂Cl₂ / 1.67 h / 0 - 20 °C

2: 68 percent / di(tert-butyl)pyridine; triflic anhydride / CH₂Cl₂ / 1.25 h / -78 °C

3: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; water / CH₂Cl₂ / 0.75 h

4: 771 mg / 4-(dimethylamino)pyridine / CH₂Cl₂ / 2.08 h / 0 - 20 °C

With triethylsilane; dmap; trifluorormethanesulfonic acid; trifluoromethylsulfonic anhydride; di(tert-butyl)pyridine; water; trifluoromethanesulfonic acid anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane;
DOI:10.1021/ol035887t