allyl 4,6-di-O-benzyl-2-deoxy-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Base Information

Chemical Name:allyl 4,6-di-O-benzyl-2-deoxy-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
CAS No.:188583-17-7
Molecular Formula:C₂₉H₃₁Cl₆NO₉
Molecular Weight:750.284
Hs Code.:

Synonyms:allyl 4,6-di-O-benzyl-2-deoxy-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

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Chemical Property of allyl 4,6-di-O-benzyl-2-deoxy-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

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Technology Process of allyl 4,6-di-O-benzyl-2-deoxy-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

There total 4 articles about allyl 4,6-di-O-benzyl-2-deoxy-3-O-(2,2,2-trichloroethoxycarbonyl)-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: 98.0%

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 129253-51-6
allyl 2-deoxy-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

: 188583-17-7
allyl 4,6-di-O-benzyl-2-deoxy-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Guidance literature:: With trifluorormethanesulfonic acid; In dichloromethane; cyclohexane; for 20h; Ambient temperature;
DOI:10.1248/cpb.45.312

Reference yield:

: 188583-14-4
allyl-2-N-Troc-2-deoxy-α-D-glucopyranoside

: 188583-17-7
allyl 4,6-di-O-benzyl-2-deoxy-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 94 percent / p-TsOH / dimethylformamide / 18 h / Ambient temperature

2: 75 percent / 4-dimethylaminopyridine, pyridine / CH₂Cl₂ / 20 h / Ambient temperature

3: 94 percent / 68percent aq. AcOH / 5 h / Ambient temperature

4: 98 percent / CF₃SO₃H / CH₂Cl₂; cyclohexane / 20 h / Ambient temperature

With pyridine; dmap; trifluorormethanesulfonic acid; toluene-4-sulfonic acid; acetic acid; In dichloromethane; cyclohexane; N,N-dimethyl-formamide;
DOI:10.1248/cpb.45.312

Reference yield:

: 188583-15-5
allyl 2-deoxy-4,6-O-p-methoxybenzylidene-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

: 188583-17-7
allyl 4,6-di-O-benzyl-2-deoxy-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 75 percent / 4-dimethylaminopyridine, pyridine / CH₂Cl₂ / 20 h / Ambient temperature

2: 94 percent / 68percent aq. AcOH / 5 h / Ambient temperature

3: 98 percent / CF₃SO₃H / CH₂Cl₂; cyclohexane / 20 h / Ambient temperature

With pyridine; dmap; trifluorormethanesulfonic acid; acetic acid; In dichloromethane; cyclohexane;
DOI:10.1248/cpb.45.312