p-methoxyphenyl 6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-4-(2,2,2-trichloroethoxycarbonylamino)-α-D-erythro-hex-3-enopyranoside

Base Information

Chemical Name:p-methoxyphenyl 6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-4-(2,2,2-trichloroethoxycarbonylamino)-α-D-erythro-hex-3-enopyranoside
CAS No.:400054-11-7
Molecular Formula:C₂₂H₃₂Cl₃NO₆Si
Molecular Weight:540.944
Hs Code.:

Synonyms:p-methoxyphenyl 6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-4-(2,2,2-trichloroethoxycarbonylamino)-α-D-erythro-hex-3-enopyranoside

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Chemical Property of p-methoxyphenyl 6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-4-(2,2,2-trichloroethoxycarbonylamino)-α-D-erythro-hex-3-enopyranoside

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Technology Process of p-methoxyphenyl 6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-4-(2,2,2-trichloroethoxycarbonylamino)-α-D-erythro-hex-3-enopyranoside

There total 12 articles about p-methoxyphenyl 6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-4-(2,2,2-trichloroethoxycarbonylamino)-α-D-erythro-hex-3-enopyranoside 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: 75.0%

: 115-20-8
1,1,1-trichloroethanol

: 755011-68-8
carbamic acid 6-(tert-butyl-dimethyl-silanyloxymethyl)-2-(4-methoxy-phenoxy)-3,6-dihydro-2H-pyran-3-yl ester

: 400054-11-7
p-methoxyphenyl 6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-4-(2,2,2-trichloroethoxycarbonylamino)-α-D-erythro-hex-3-enopyranoside

Guidance literature:: carbamic acid 6-(tert-butyl-dimethyl-silanyloxymethyl)-2-(4-methoxy-phenoxy)-3,6-dihydro-2H-pyran-3-yl ester; With carbon tetrabromide; triethylamine; triphenylphosphine; In dichloromethane; at -40 ℃;

In dichloromethane; at 0 ℃; for 1h;

1,1,1-trichloroethanol; In dichloromethane; at 0 - 20 ℃;
DOI:10.1055/s-2001-18108

Reference yield:

: 400054-04-8
p-methoxyphenyl 3,4-dideoxy-α-D-erythro-hex-3-enopyranoside

: 400054-11-7
p-methoxyphenyl 6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-4-(2,2,2-trichloroethoxycarbonylamino)-α-D-erythro-hex-3-enopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 75 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 20 °C

2.1: CH₂Cl₂ / 1 h / 0 °C

2.2: 25.6 g / aq. K₂CO₃ / methanol / 2.5 h / 20 °C

3.1: CBr₄; PPh₃; Et₃N / CH₂Cl₂ / 0.5 h / -40 - 0 °C

4.1: CH₂Cl₂ / 1 h / 0 °C

5.1: 10.1 g / CH₂Cl₂ / 0 - 20 °C

With dmap; carbon tetrabromide; triethylamine; triphenylphosphine; In dichloromethane;
DOI:10.1002/chem.200305358

Reference yield:

: 400054-02-6
p-methoxyphenyl 2,4,6-triacetyl-3-deoxy-α-D-erythro-hex-2-enopyranoside

: 400054-11-7
p-methoxyphenyl 6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-4-(2,2,2-trichloroethoxycarbonylamino)-α-D-erythro-hex-3-enopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: 84 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

2.1: 75 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 20 °C

3.1: CH₂Cl₂ / 1 h / 0 °C

3.2: 25.6 g / aq. K₂CO₃ / methanol / 2.5 h / 20 °C

4.1: CBr₄; PPh₃; Et₃N / CH₂Cl₂ / 0.5 h / -40 - 0 °C

5.1: CH₂Cl₂ / 1 h / 0 °C

6.1: 10.1 g / CH₂Cl₂ / 0 - 20 °C

With dmap; lithium aluminium tetrahydride; carbon tetrabromide; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane;
DOI:10.1002/chem.200305358