Allyl 6-O-benzoyl-4-O-benzyl-2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloro-tert-butoxycarbonylamino)-β-D-glucopyranoside

Base Information

• Chemical Name: Allyl 6-O-benzoyl-4-O-benzyl-2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloro-tert-butoxycarbonylamino)-β-D-glucopyranoside
• CAS No.: 103559-30-4
• Molecular Formula: C₃₃H₃₇Cl₆NO₁₀
• Molecular Weight: 820.375

Synonyms:Allyl 6-O-benzoyl-4-O-benzyl-2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloro-tert-butoxycarbonylamino)-β-D-glucopyranoside

Chemical Property of Allyl 6-O-benzoyl-4-O-benzyl-2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloro-tert-butoxycarbonylamino)-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Allyl 6-O-benzoyl-4-O-benzyl-2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloro-tert-butoxycarbonylamino)-β-D-glucopyranoside

There total 4 articles about Allyl 6-O-benzoyl-4-O-benzyl-2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloro-tert-butoxycarbonylamino)-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:

2,2,2-trichloro-1,1-dimethylethoxychloroformate (66270-36-8) → Allyl 6-O-benzoyl-4-O-benzyl-2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloro-tert-butoxycarbonylamino)-β-D-glucopyranoside (103559-30-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / 4-dimethylaminopyridine / pyridine / 12 h / Ambient temperature

2: 90 percent / 90percent acetic acid / 0.25 h / 90 °C

3: 75 percent / pyridine; tetrahydrofuran / 9 h / 0 °C

4: 49 percent / trifluoromethanesulfonic acid / 15 h / Ambient temperature

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

DOI:10.1016/S0040-4039(00)84384-1

Reference yield:

Allyl 2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside (99519-05-8) → Allyl 6-O-benzoyl-4-O-benzyl-2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloro-tert-butoxycarbonylamino)-β-D-glucopyranoside (103559-30-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / 4-dimethylaminopyridine / pyridine / 12 h / Ambient temperature

2: 90 percent / 90percent acetic acid / 0.25 h / 90 °C

3: 75 percent / pyridine; tetrahydrofuran / 9 h / 0 °C

4: 49 percent / trifluoromethanesulfonic acid / 15 h / Ambient temperature

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

DOI:10.1016/S0040-4039(00)84384-1

Reference yield:

Allyl 2-deoxy-4,6-O-isopropylidene-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloro-tert-butoxycarbonylamino)-β-D-glucopyranoside (103559-27-9) → Allyl 6-O-benzoyl-4-O-benzyl-2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloro-tert-butoxycarbonylamino)-β-D-glucopyranoside (103559-30-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / 90percent acetic acid / 0.25 h / 90 °C

2: 75 percent / pyridine; tetrahydrofuran / 9 h / 0 °C

3: 49 percent / trifluoromethanesulfonic acid / 15 h / Ambient temperature

With acetic acid; trifluorormethanesulfonic acid; In tetrahydrofuran; pyridine;

DOI:10.1016/S0040-4039(00)84384-1

upstream raw materials:

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

Allyl 2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

Allyl 2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloro-tert-butoxycarbonylamino)-β-D-glucopyranoside

Allyl 2-deoxy-4,6-O-isopropylidene-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloro-tert-butoxycarbonylamino)-β-D-glucopyranoside

Downstream raw materials:

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

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

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