N-{2-(tert-butyldiphenylsilyloxy)ethyl}-N-{2-[6-O-benzyl-2-deoxy-3-O-((R)-3-tetradecanoyloxytetradecanoyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyloxy]ethyl}-2,2,2-trichloroethoxymethanamide

Base Information

Chemical Name:N-{2-(tert-butyldiphenylsilyloxy)ethyl}-N-{2-[6-O-benzyl-2-deoxy-3-O-((R)-3-tetradecanoyloxytetradecanoyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyloxy]ethyl}-2,2,2-trichloroethoxymethanamide
CAS No.:1428739-44-9
Molecular Formula:C₆₇H₁₀₀Cl₆N₂O₁₃Si
Molecular Weight:1382.34
Hs Code.:

N-{2-(tert-butyldiphenylsilyloxy)ethyl}-N-{2-[6-O-benzyl-2-deoxy-3-O-((R)-3-tetradecanoyloxytetradecanoyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyloxy]ethyl}-2,2,2-trichloroethoxymethanamide

Synonyms:N-{2-(tert-butyldiphenylsilyloxy)ethyl}-N-{2-[6-O-benzyl-2-deoxy-3-O-((R)-3-tetradecanoyloxytetradecanoyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyloxy]ethyl}-2,2,2-trichloroethoxymethanamide

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Chemical Property of N-{2-(tert-butyldiphenylsilyloxy)ethyl}-N-{2-[6-O-benzyl-2-deoxy-3-O-((R)-3-tetradecanoyloxytetradecanoyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyloxy]ethyl}-2,2,2-trichloroethoxymethanamide

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Technology Process of N-{2-(tert-butyldiphenylsilyloxy)ethyl}-N-{2-[6-O-benzyl-2-deoxy-3-O-((R)-3-tetradecanoyloxytetradecanoyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyloxy]ethyl}-2,2,2-trichloroethoxymethanamide

There total 6 articles about N-{2-(tert-butyldiphenylsilyloxy)ethyl}-N-{2-[6-O-benzyl-2-deoxy-3-O-((R)-3-tetradecanoyloxytetradecanoyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyloxy]ethyl}-2,2,2-trichloroethoxymethanamide 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: 87.0%

: N-{2-(tert-butyldiphenylsilyloxy)ethyl}-N-{2-[4,6-O-benzylidene-2-deoxy-3-O-((R)-3-tetradecanoyloxytetradecanoyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyloxy]ethyl}-2,2,2-trichloroethoxymethanamide

: 1428739-44-9
N-{2-(tert-butyldiphenylsilyloxy)ethyl}-N-{2-[6-O-benzyl-2-deoxy-3-O-((R)-3-tetradecanoyloxytetradecanoyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyloxy]ethyl}-2,2,2-trichloroethoxymethanamide

Guidance literature:: With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; at 0 ℃; regioselective reaction; Molecular sieve; Inert atmosphere;
DOI:10.1016/j.bmc.2013.02.024

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1428739-44-9
N-{2-(tert-butyldiphenylsilyloxy)ethyl}-N-{2-[6-O-benzyl-2-deoxy-3-O-((R)-3-tetradecanoyloxytetradecanoyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyloxy]ethyl}-2,2,2-trichloroethoxymethanamide

Guidance literature:: Multi-step reaction with 6 steps

1: triethylamine / dichloromethane / 3 h / 20 °C

2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1.5 h / 20 °C / Molecular sieve; Inert atmosphere

3: guanidine nitrate; sodium methylate / dichloromethane; methanol / 3 h / 20 °C

4: toluene-4-sulfonic acid / 2 h / 20 °C

5: dmap; diisopropyl-carbodiimide / dichloromethane / 4 h / 20 °C

6: sodium cyanoborohydride; hydrogenchloride / tetrahydrofuran; diethyl ether / 0 °C / Molecular sieve; Inert atmosphere

With hydrogenchloride; dmap; trimethylsilyl trifluoromethanesulfonate; sodium methylate; guanidine nitrate; sodium cyanoborohydride; toluene-4-sulfonic acid; triethylamine; diisopropyl-carbodiimide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1016/j.bmc.2013.02.024

Reference yield:

: 1428739-40-5
N-{2-(tert-butyldiphenylsilyloxy)ethyl}-N-{2-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyloxy]ethyl}-2,2,2-trichloroethoxymethanamide

: 1428739-44-9
N-{2-(tert-butyldiphenylsilyloxy)ethyl}-N-{2-[6-O-benzyl-2-deoxy-3-O-((R)-3-tetradecanoyloxytetradecanoyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyloxy]ethyl}-2,2,2-trichloroethoxymethanamide

Guidance literature:: Multi-step reaction with 4 steps

1: guanidine nitrate; sodium methylate / dichloromethane; methanol / 3 h / 20 °C

2: toluene-4-sulfonic acid / 2 h / 20 °C

3: dmap; diisopropyl-carbodiimide / dichloromethane / 4 h / 20 °C

4: sodium cyanoborohydride; hydrogenchloride / tetrahydrofuran; diethyl ether / 0 °C / Molecular sieve; Inert atmosphere

With hydrogenchloride; dmap; sodium methylate; guanidine nitrate; sodium cyanoborohydride; toluene-4-sulfonic acid; diisopropyl-carbodiimide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1016/j.bmc.2013.02.024