Allyl 4-O-benzyl-2-deoxy-6-O-(p-nitrobenzoyl)-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Base Information

• Chemical Name: Allyl 4-O-benzyl-2-deoxy-6-O-(p-nitrobenzoyl)-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
• CAS No.: 134040-54-3
• Molecular Formula: C₃₁H₃₂Cl₆N₂O₁₂
• Molecular Weight: 837.319

Synonyms:Allyl 4-O-benzyl-2-deoxy-6-O-(p-nitrobenzoyl)-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Chemical Property of Allyl 4-O-benzyl-2-deoxy-6-O-(p-nitrobenzoyl)-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of Allyl 4-O-benzyl-2-deoxy-6-O-(p-nitrobenzoyl)-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

There total 5 articles about Allyl 4-O-benzyl-2-deoxy-6-O-(p-nitrobenzoyl)-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-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: 86.1%

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) + Allyl 2-deoxy-6-O-(p-nitrobenzoyl)-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (134040-53-2) → Allyl 4-O-benzyl-2-deoxy-6-O-(p-nitrobenzoyl)-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (134040-54-3)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; Ambient temperature;

DOI:10.1248/cpb.39.288

Reference yield:

2,2,2-trichloro-1,1-dimethylethoxychloroformate (66270-36-8) → Allyl 4-O-benzyl-2-deoxy-6-O-(p-nitrobenzoyl)-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (134040-54-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 97.3 percent / pyridine, 4-dimethylaminopyridine / CH₂Cl₂ / Ambient temperature

2: 97 percent / 90 percent aq. acetic acid / 90 °C

3: 93.6 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

4: 86.1 percent / trifluoromethanesulfonic acid / CH₂Cl₂ / Ambient temperature

With pyridine; dmap; trifluorormethanesulfonic acid; acetic acid; In dichloromethane;

DOI:10.1248/cpb.39.288

Reference yield:

allyl 2-deoxy-4,6-O-isopropylidene-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (97562-24-8) → Allyl 4-O-benzyl-2-deoxy-6-O-(p-nitrobenzoyl)-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (134040-54-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 97.3 percent / pyridine, 4-dimethylaminopyridine / CH₂Cl₂ / Ambient temperature

2: 97 percent / 90 percent aq. acetic acid / 90 °C

3: 93.6 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

4: 86.1 percent / trifluoromethanesulfonic acid / CH₂Cl₂ / Ambient temperature

With pyridine; dmap; trifluorormethanesulfonic acid; acetic acid; In dichloromethane;

DOI:10.1248/cpb.39.288

upstream raw materials:

O-benzyl 2,2,2-trichloroacetimidate

Allyl 2-deoxy-6-O-(p-nitrobenzoyl)-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

2,2,2-trichloro-1,1-dimethylethoxychloroformate

allyl 2-deoxy-4,6-O-isopropylidene-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Downstream raw materials:

Allyl 4-O-benzyl-2-deoxy-6-O-(3,4,6-tri-O-acetyl-2-chloroacetylamino-2-deoxy-β-D-glucopyranosyl)-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Allyl 4-O-benzyl-6-O-(2-chloroacetylamino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Allyl 4-O-benzyl-6-O-(2-chloroacetylamino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Allyl 6-O-(2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-4-O-benzyl-2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

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