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

Base Information

• Chemical Name: 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
• CAS No.: 937394-25-7
• Molecular Formula: C₄₂H₄₀Cl₃N₂O₁₂P
• Molecular Weight: 902.119

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 7 articles about 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 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: 92.0%

C40H40NO12P (937394-55-3) + trichloroacetonitrile (545-06-2) → 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 (937394-25-7)

Guidance literature:

With sodium hydride; In dichloromethane; at 20 ℃; for 0.833333h;

DOI:10.1021/ja068922a

Reference yield:

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) → 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 (937394-25-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / HF*pyridine / tetrahydrofuran / 12 h / 20 °C

2: 92 percent / NaH / CH₂Cl₂ / 0.83 h / 20 °C

With sodium hydride; pyridine hydrogenfluoride; In tetrahydrofuran; 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) → 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 (937394-25-7)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: 98 percent / HF*pyridine / tetrahydrofuran / 12 h / 20 °C

4: 92 percent / NaH / CH₂Cl₂ / 0.83 h / 20 °C

With sodium hydride; pyridine hydrogenfluoride; acetic acid; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja068922a

upstream raw materials:

C₄₀H₄₀NO₁₂P

trichloroacetonitrile

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

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

Downstream raw materials:

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

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-[(R)-3-dodecanoyloxy-tetradecanoylamino]-β-D-glucopyranosyl}-2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranoside

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