phenyl 2-deoxy-4,6-O-p-methoxybenzylidene-3-O-(tetradecanoyl)-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

Base Information

Chemical Name:phenyl 2-deoxy-4,6-O-p-methoxybenzylidene-3-O-(tetradecanoyl)-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside
CAS No.:263010-65-7
Molecular Formula:C₃₇H₅₀Cl₃NO₈S
Molecular Weight:775.231
Hs Code.:

Synonyms:phenyl 2-deoxy-4,6-O-p-methoxybenzylidene-3-O-(tetradecanoyl)-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

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Chemical Property of phenyl 2-deoxy-4,6-O-p-methoxybenzylidene-3-O-(tetradecanoyl)-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

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Technology Process of phenyl 2-deoxy-4,6-O-p-methoxybenzylidene-3-O-(tetradecanoyl)-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

There total 1 articles about phenyl 2-deoxy-4,6-O-p-methoxybenzylidene-3-O-(tetradecanoyl)-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-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: 96.0%

: 112-64-1
tetradecanoyl chloride

: 188583-25-7
phenyl 2-[(2,2,2-trichloroethoxy)carbonyl]amino-4,6-O-p-methoxybenzylidene-2-deoxy-1-thio-β-D-glucopyranoside

: 263010-65-7
phenyl 2-deoxy-4,6-O-p-methoxybenzylidene-3-O-(tetradecanoyl)-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

Guidance literature:: With pyridine; dmap; In dichloromethane; at 20 ℃; for 10h;
DOI:10.1248/cpb.48.32

Reference yield: 98.0%

: 263010-65-7
phenyl 2-deoxy-4,6-O-p-methoxybenzylidene-3-O-(tetradecanoyl)-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

: 888017-27-4
Tetradecanoic acid (2R,3S,4R,5R,6S)-3-hydroxy-2-hydroxymethyl-6-phenylsulfanyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester

Guidance literature:: With acetic acid; at 20 ℃; for 10h;
DOI:10.1248/cpb.48.32

Reference yield:

: 263010-65-7
phenyl 2-deoxy-4,6-O-p-methoxybenzylidene-3-O-(tetradecanoyl)-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

: Tetradecanoic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-amino-6-((S)-2-benzyloxycarbonyl-2-tetradecanoylamino-ethoxy)-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / 90 percent aq. AcOH / 10 h / 20 °C

2: 93 percent / pyridine / 5 h / 20 °C

3: 79 percent / NBS; I₂; TBAOTf / CH₂Cl₂

4: Zn; AcOH / 40 - 50 °C

With pyridine; N-Bromosuccinimide; iodine; tetrabutylammonium trifluoromethylsulfonate; acetic acid; zinc; In dichloromethane; 1: Hydrolysis / 2: Acetylation / 3: glycosidation / 4: Hydrogenolysis;
DOI:10.1248/cpb.48.32