2-(trimethylsilyl)ethyl (3-O-allyl-2-azido-4,6-O-benzylidene-2-deoxy-β-D-mannopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-glucopyranoside

Base Information

Chemical Name:2-(trimethylsilyl)ethyl (3-O-allyl-2-azido-4,6-O-benzylidene-2-deoxy-β-D-mannopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-glucopyranoside
CAS No.:499126-60-2
Molecular Formula:C₄₈H₅₇N₃O₁₁Si
Molecular Weight:880.08
Hs Code.:

Synonyms:2-(trimethylsilyl)ethyl (3-O-allyl-2-azido-4,6-O-benzylidene-2-deoxy-β-D-mannopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-glucopyranoside

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Chemical Property of 2-(trimethylsilyl)ethyl (3-O-allyl-2-azido-4,6-O-benzylidene-2-deoxy-β-D-mannopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-glucopyranoside

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Technology Process of 2-(trimethylsilyl)ethyl (3-O-allyl-2-azido-4,6-O-benzylidene-2-deoxy-β-D-mannopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-glucopyranoside

There total 6 articles about 2-(trimethylsilyl)ethyl (3-O-allyl-2-azido-4,6-O-benzylidene-2-deoxy-β-D-mannopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-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:

: Benzoic acid (2R,3R,4S,5R,6R)-5-((2R,4aR,6S,7R,8S,8aR)-8-allyloxy-2-phenyl-7-trifluoromethanesulfonyloxy-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

: 499126-60-2
2-(trimethylsilyl)ethyl (3-O-allyl-2-azido-4,6-O-benzylidene-2-deoxy-β-D-mannopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-glucopyranoside

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 70 ℃; for 3h;
DOI:10.1016/S0008-6215(02)00263-X

Reference yield:

: 20701-61-5,56119-28-9,131564-36-8,142924-31-0,151123-92-1,141899-53-8
ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside

: 499126-60-2
2-(trimethylsilyl)ethyl (3-O-allyl-2-azido-4,6-O-benzylidene-2-deoxy-β-D-mannopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: Bu₂SnO / methanol / 1 h / Heating

1.2: 67 percent / CsF / dimethylformamide / 20 °C

2.1: 97 percent / pyridine / 1 h / 20 °C

3.1: 79 percent / NIS; TfOH / CH₂Cl₂ / 1 h / -30 °C

4.1: 67 percent / Mg(OMe)2 / methanol; CH₂Cl₂ / 3 h / 20 °C / pH 12

5.1: pyridine / CH₂Cl₂ / 20 h / 0 °C

6.1: 208 mg / NaN₃ / dimethylformamide / 3 h / 70 °C

With pyridine; N-iodo-succinimide; sodium azide; trifluorormethanesulfonic acid; di(n-butyl)tin oxide; magnesium methanolate; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(02)00263-X

Reference yield:

: 499126-40-8
ethyl 3-O-allyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

: 499126-60-2
2-(trimethylsilyl)ethyl (3-O-allyl-2-azido-4,6-O-benzylidene-2-deoxy-β-D-mannopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / pyridine / 1 h / 20 °C

2: 79 percent / NIS; TfOH / CH₂Cl₂ / 1 h / -30 °C

3: 67 percent / Mg(OMe)2 / methanol; CH₂Cl₂ / 3 h / 20 °C / pH 12

4: pyridine / CH₂Cl₂ / 20 h / 0 °C

5: 208 mg / NaN₃ / dimethylformamide / 3 h / 70 °C

With pyridine; N-iodo-succinimide; sodium azide; trifluorormethanesulfonic acid; magnesium methanolate; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(02)00263-X