allyl 6-O-benzyl-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-tetradecanoyl-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Base Information

Chemical Name:allyl 6-O-benzyl-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-tetradecanoyl-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
CAS No.:828939-48-6
Molecular Formula:C₄₇H₆₃Cl₃NO₁₁P
Molecular Weight:955.35
Hs Code.:

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

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

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

There total 5 articles about allyl 6-O-benzyl-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-tetradecanoyl-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: 78.0%

: 108549-23-1
Dibenzyl N,N-diisopropylphosphoramidite

: 828939-46-4
allyl 6-O-benzyl-2-deoxy-3-O-tetradecanoyl-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

: 828939-48-6
allyl 6-O-benzyl-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-tetradecanoyl-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Guidance literature:: Dibenzyl N,N-diisopropylphosphoramidite; allyl 6-O-benzyl-2-deoxy-3-O-tetradecanoyl-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside; With 1H-tetrazole; In dichloromethane; acetonitrile; for 0.5h;

With tert.-butylhydroperoxide; In dichloromethane; acetonitrile; at 0 ℃; for 6h;
DOI:10.1016/j.tet.2004.10.017

Reference yield: 6.0%

: 108549-23-1
Dibenzyl N,N-diisopropylphosphoramidite

: 828939-46-4
allyl 6-O-benzyl-2-deoxy-3-O-tetradecanoyl-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

: allyl 6-O-benzyl-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-tetradecyl-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

: 828939-48-6
allyl 6-O-benzyl-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-tetradecanoyl-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Guidance literature:: Dibenzyl N,N-diisopropylphosphoramidite; allyl 6-O-benzyl-2-deoxy-3-O-tetradecanoyl-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside; With 1H-tetrazole; borane dimethylamine complex; In dichloromethane; acetonitrile; for 0.5h;

With tert.-butylhydroperoxide; In dichloromethane; acetonitrile; at 0 ℃; for 6h;
DOI:10.1016/j.tet.2004.10.017

Reference yield:

: 112-64-1
tetradecanoyl chloride

: 828939-48-6
allyl 6-O-benzyl-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-tetradecanoyl-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 95 percent / pyridine / tetrahydrofuran / 1 h

2.1: 92 percent / triethylsilane; trifluoromethanesulfonic acid; molecular sieves 0.4 nm / CH₂Cl₂ / 0.67 h / -78 °C

3.1: 1H-tetrazole; borane-dimethylamine complex / CH₂Cl₂; acetonitrile / 0.5 h

3.2: 44 percent / tert-butylhydroperoxide / CH₂Cl₂; acetonitrile / 6 h / 0 °C

With pyridine; 1H-tetrazole; triethylsilane; trifluorormethanesulfonic acid; 4 A molecular sieve; borane dimethylamine complex; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1016/j.tet.2004.10.017