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

Base Information

• Chemical Name: 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
• CAS No.: 937394-24-6
• Molecular Formula: C₄₆H₅₄NO₁₂PSi
• Molecular Weight: 871.994

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 9 articles about 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 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: 73.0%

C31H44NO10PSi + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → 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 (937394-24-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 5h;

Reference yield:

tert-butyldimethylsilyl 3-O-allyloxycarbonyl-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside (937394-22-4) → 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 (937394-24-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1H-tetrazole / CH₂Cl₂ / 0.25 h / 20 °C

1.2: 89 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 0.33 h / -20 °C

2.1: acetic acid; zinc / CH₂Cl₂ / 2 h / 20 °C

3.1: 1.45 g / N,N-diisopropylethylamine / CH₂Cl₂ / 5 h / 0 - 20 °C

With 1H-tetrazole; acetic acid; N-ethyl-N,N-diisopropylamine; zinc; In dichloromethane;

DOI:10.1021/ja068922a

Reference yield:

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) → 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 (937394-24-6)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid; zinc / CH₂Cl₂ / 2 h / 20 °C

2: 1.45 g / N,N-diisopropylethylamine / CH₂Cl₂ / 5 h / 0 - 20 °C

With acetic acid; N-ethyl-N,N-diisopropylamine; zinc; In dichloromethane;

DOI:10.1021/ja068922a

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

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

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

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

Downstream raw materials:

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

C₄₄H₅₉N₄O₁₄PSi

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