allyl 4,6-O-benzylidene-3-O-[(R)-3-(benzyloxy)tetradecanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Base Information

Chemical Name:allyl 4,6-O-benzylidene-3-O-[(R)-3-(benzyloxy)tetradecanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
CAS No.:185801-00-7
Molecular Formula:C₄₀H₅₄Cl₃NO₉
Molecular Weight:799.229
Hs Code.:

Synonyms:allyl 4,6-O-benzylidene-3-O-[(R)-3-(benzyloxy)tetradecanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

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Chemical Property of allyl 4,6-O-benzylidene-3-O-[(R)-3-(benzyloxy)tetradecanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

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Technology Process of allyl 4,6-O-benzylidene-3-O-[(R)-3-(benzyloxy)tetradecanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

There total 3 articles about allyl 4,6-O-benzylidene-3-O-[(R)-3-(benzyloxy)tetradecanoyl]-2-deoxy-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: 89.0%

: 87357-67-3
(R)-3-benzyloxytetradecanoic acid

: 183388-21-8
allyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

: 185801-00-7
allyl 4,6-O-benzylidene-3-O-[(R)-3-(benzyloxy)tetradecanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1016/j.bmc.2006.05.051

Reference yield:

: 172490-46-9
2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose

: 185801-00-7
allyl 4,6-O-benzylidene-3-O-[(R)-3-(benzyloxy)tetradecanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: hydrogen chloride / 0.33 h / Heating

2: 12.3 g / (+)-camphor-10-sulfonic acid / tetrahydrofuran / 3 h / Heating

3: 81 percent / dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / 20 °C

With hydrogenchloride; dmap; (+)-10-camphorsulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 1: Etherification / 2: Cyclization / 3: Esterification;
DOI:10.1246/bcsj.70.1435

Reference yield:

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

: 185801-00-7
allyl 4,6-O-benzylidene-3-O-[(R)-3-(benzyloxy)tetradecanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 12.3 g / (+)-camphor-10-sulfonic acid / tetrahydrofuran / 3 h / Heating

2: 81 percent / dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / 20 °C

With dmap; (+)-10-camphorsulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 1: Cyclization / 2: Esterification;
DOI:10.1246/bcsj.70.1435