t-butyldimethylsilyl 3-O-allyloxycarbonyl-2-azido-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3yl)-β-D-glucopyranoside

Base Information

• Chemical Name: t-butyldimethylsilyl 3-O-allyloxycarbonyl-2-azido-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3yl)-β-D-glucopyranoside
• CAS No.: 937394-23-5
• Molecular Formula: C₃₁H₄₂N₃O₁₀PSi
• Molecular Weight: 675.748

Synonyms:t-butyldimethylsilyl 3-O-allyloxycarbonyl-2-azido-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3yl)-β-D-glucopyranoside

Chemical Property of t-butyldimethylsilyl 3-O-allyloxycarbonyl-2-azido-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3yl)-β-D-glucopyranoside

Chemical Property:

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Technology Process of t-butyldimethylsilyl 3-O-allyloxycarbonyl-2-azido-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3yl)-β-D-glucopyranoside

There total 7 articles about t-butyldimethylsilyl 3-O-allyloxycarbonyl-2-azido-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3yl)-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: 89.0%

tert-butyldimethylsilyl 3-O-allyloxycarbonyl-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside (937394-22-4) + N,N-diethyl-1,5-dihydro-3H-2,4,3-benzodioxaphosphepin-3-amine (82372-35-8) → t-butyldimethylsilyl 3-O-allyloxycarbonyl-2-azido-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3yl)-β-D-glucopyranoside (937394-23-5)

Guidance literature:

tert-butyldimethylsilyl 3-O-allyloxycarbonyl-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside; N,N-diethyl-1,5-dihydro-3H-2,4,3-benzodioxaphosphepin-3-amine; With 1H-tetrazole; In dichloromethane; at 20 ℃; for 0.25h;

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -20 ℃; for 0.333333h; Further stages.;

DOI:10.1021/ja068922a

Reference yield:

tert-butyldimethylsilyl 3-O-allyloxycarbonyl-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (937394-20-2) → t-butyldimethylsilyl 3-O-allyloxycarbonyl-2-azido-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3yl)-β-D-glucopyranoside (937394-23-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 88 percent / HCl; NaCNBH₄ / tetrahydrofuran; diethyl ether / 0.5 h / 20 °C / pH 5

2.1: 1H-tetrazole / CH₂Cl₂ / 0.25 h / 20 °C

2.2: 89 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 0.33 h / -20 °C

With 1H-tetrazole; hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/ja068922a

Reference yield:

2-azido-4,6-O-benzylidene-2-deoxyl-1-O-tert-butyldimethylsilyl-β-D-glucopyranoside (138923-10-1) → t-butyldimethylsilyl 3-O-allyloxycarbonyl-2-azido-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3yl)-β-D-glucopyranoside (937394-23-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 88 percent / N,N,N',N'-tetramethylethylenediamine / CH₂Cl₂ / 10 h / 20 °C

2.1: 88 percent / HCl; NaCNBH₄ / tetrahydrofuran; diethyl ether / 0.5 h / 20 °C / pH 5

3.1: 1H-tetrazole / CH₂Cl₂ / 0.25 h / 20 °C

3.2: 89 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 0.33 h / -20 °C

With 1H-tetrazole; hydrogenchloride; N,N,N,N,-tetramethylethylenediamine; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/ja068922a

upstream raw materials:

tert-butyldimethylsilyl 3-O-allyloxycarbonyl-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside

N,N-diethyl-1,5-dihydro-3H-2,4,3-benzodioxaphosphepin-3-amine

tert-butyldimethylsilyl 3-O-allyloxycarbonyl-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

2-azido-4,6-O-benzylidene-2-deoxyl-1-O-tert-butyldimethylsilyl-β-D-glucopyranoside

Downstream raw materials:

t-butyldimethylsilyl 3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3yl)-2-(9-fluorenylmethoxycarbonylamino)-β-D-glucopyranoside

C₄₀H₄₀NO₁₂P

3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3yl)-2-(9-fluorenylmethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate

tert-butyldimethylsilyl-6-O-[3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(9-fluorenylmethoxycarbonylamino)-β-D-glucopyranosyl]-2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranoside

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