ethyl 4,6-O-benzylidene-3-O-tert-butyldiphenylsilyl-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: ethyl 4,6-O-benzylidene-3-O-tert-butyldiphenylsilyl-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside
• CAS No.: 457931-12-3
• Molecular Formula: C₃₉H₄₆O₆SSi
• Molecular Weight: 670.942

Synonyms:ethyl 4,6-O-benzylidene-3-O-tert-butyldiphenylsilyl-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside

Chemical Property of ethyl 4,6-O-benzylidene-3-O-tert-butyldiphenylsilyl-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside

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Technology Process of ethyl 4,6-O-benzylidene-3-O-tert-butyldiphenylsilyl-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside

There total 3 articles about ethyl 4,6-O-benzylidene-3-O-tert-butyldiphenylsilyl-2-O-p-methoxybenzyl-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: 91.0%

tert-butylchlorodiphenylsilane (58479-61-1) + ethyl 4,6-O-benzylidene-2-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside (503830-08-8) → ethyl 4,6-O-benzylidene-3-O-tert-butyldiphenylsilyl-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside (457931-12-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 50 ℃; for 18h;

DOI:10.1016/S0008-6215(02)00295-1

Reference yield:

p-methoxybenzyl chloride (824-94-2) → ethyl 4,6-O-benzylidene-3-O-tert-butyldiphenylsilyl-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside (457931-12-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / aq. NaOH; Bu₄NBr / CH₂Cl₂ / 30 h / Heating

2: 91 percent / imidazole / dimethylformamide / 18 h / 50 °C

With 1H-imidazole; sodium hydroxide; tetrabutylammomium bromide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(02)00295-1

Reference yield:

S-ethyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside (142924-31-0) → ethyl 4,6-O-benzylidene-3-O-tert-butyldiphenylsilyl-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside (457931-12-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / aq. NaOH; Bu₄NBr / CH₂Cl₂ / 30 h / Heating

2: 91 percent / imidazole / dimethylformamide / 18 h / 50 °C

With 1H-imidazole; sodium hydroxide; tetrabutylammomium bromide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(02)00295-1

upstream raw materials:

tert-butylchlorodiphenylsilane

ethyl 4,6-O-benzylidene-2-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside

p-methoxybenzyl chloride

S-ethyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Downstream raw materials:

{7-[(4,5-bis-benzyloxy-2-benzyloxymethyl-6-octyloxy-tetrahydro-pyran-3-yloxy)-(4-methoxy-phenyl)-methoxy]-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-tert-butyl-diphenyl-silane

7-[[4,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-(4-methoxy-phenyl)-methoxy]-8-(tert-butyl-diphenyl-silanyloxy)-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

2-(trimethylsilyl)ethyl 2-O-benzoyl-4,6-O-benzylidene-3-O-tert-butyldiphenylsilyl-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

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