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

Base Information

Chemical Name:allyl 4,6-O-benzylidene-3-O-[(S)-3-(benzyloxy)tetradecanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
CAS No.:172371-05-0
Molecular Formula:C₄₀H₅₄Cl₃NO₉
Molecular Weight:799.229
Hs Code.:

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

There total 1 articles about allyl 4,6-O-benzylidene-3-O-[(S)-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: 76.0%

: (S)-3-(benzyloxy)tetradecanoic acid

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

: 172371-05-0
allyl 4,6-O-benzylidene-3-O-[(S)-3-(benzyloxy)tetradecanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1246/bcsj.70.1441

Reference yield: 94.0%

: 172371-05-0
allyl 4,6-O-benzylidene-3-O-[(S)-3-(benzyloxy)tetradecanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

: 192444-67-0
allyl 6-O-benzyl-3-O-[(S)-3-(benzyloxy)tetradecanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Guidance literature:: With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; for 0.166667h;
DOI:10.1246/bcsj.70.1441

Reference yield:

: 172371-05-0
allyl 4,6-O-benzylidene-3-O-[(S)-3-(benzyloxy)tetradecanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

: 6-O-benzyl-3-O-[(S)-3-(benzyloxy)tetradecanoyl]-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose

Guidance literature:: Multi-step reaction with 4 steps

1: 94 percent / sodium cyanotrihydroborate; hydrogen chloride / tetrahydrofuran / 0.17 h

2: 1H-tetrazole / CH₂Cl₂ / 0.83 h / -20 - 20 °C

3: 311 mg / m-chloroperbenzoic acid / CH₂Cl₂ / 0.67 h / -20 °C

4: 88 percent / hydrogen; iodine; water / [Ir(cod)(MePh₂P)2]PF₆ / tetrahydrofuran / 0.67 h / 20 °C

With 1H-tetrazole; hydrogenchloride; water; hydrogen; iodine; sodium cyanoborohydride; 3-chloro-benzenecarboperoxoic acid; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In tetrahydrofuran; dichloromethane; 1: Ring cleavage / 2: phosphitylation / 3: Oxidation / 4: deallylation;
DOI:10.1246/bcsj.70.1441