(2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
CAS No.:117780-27-5
Molecular Formula:C₃₉H₄₃ClO₈Si
Molecular Weight:703.304
Hs Code.:

(2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Synonyms:

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Chemical Property of (2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

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Technology Process of (2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 12 articles about (2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 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:

: 2595-07-5,821794-45-0
allyl β-D-galactopyranoside

: 117780-27-5
(2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 55.9 percent / p-toluenesulfonic acid / dimethylformamide / 5 h / Ambient temperature

2: 55.7 percent / 60 percent NaH / dimethylformamide / 1.) 1 h; 2.) 0.5 h, 0 deg C; 3.) 2.5 h, RT

3: 1.) t-BuOK; 2.) I₂, pyridine / 1.) DMSO, 60 deg C, 3 h; 2.) aq. THF, 30 min, RT

4: imidazole / dimethylformamide / 7 h / 60 °C

5: 79.3 percent / 80 percent AcOH / tetrahydrofuran / Ambient temperature

7: pyridine

8: benzenesulfonic acid / CHCl₃; methanol

9: oxalyl chloride, Et₃N / CH₂Cl₂; dimethylsulfoxide

10: Jones reagent / acetone

11: diethyl ether

With pyridine; 1H-imidazole; jones reagent; oxalyl dichloride; potassium tert-butylate; iodine; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; benzenesulfonic acid; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0008-6215(00)90828-0

Reference yield:

: 100-39-0
benzyl bromide

: 117780-27-5
(2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 55.7 percent / 60 percent NaH / dimethylformamide / 1.) 1 h; 2.) 0.5 h, 0 deg C; 3.) 2.5 h, RT

2: 1.) t-BuOK; 2.) I₂, pyridine / 1.) DMSO, 60 deg C, 3 h; 2.) aq. THF, 30 min, RT

3: imidazole / dimethylformamide / 7 h / 60 °C

4: 79.3 percent / 80 percent AcOH / tetrahydrofuran / Ambient temperature

6: pyridine

7: benzenesulfonic acid / CHCl₃; methanol

8: oxalyl chloride, Et₃N / CH₂Cl₂; dimethylsulfoxide

9: Jones reagent / acetone

10: diethyl ether

With pyridine; 1H-imidazole; jones reagent; oxalyl dichloride; potassium tert-butylate; iodine; sodium hydride; acetic acid; triethylamine; benzenesulfonic acid; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0008-6215(00)90828-0

Reference yield:

: 117780-23-1
2,3-di-O-benzyl-4,6-O-isopropylidene-D-galactopyranose

: 117780-27-5
(2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: imidazole / dimethylformamide / 7 h / 60 °C

2: 79.3 percent / 80 percent AcOH / tetrahydrofuran / Ambient temperature

4: pyridine

5: benzenesulfonic acid / CHCl₃; methanol

6: oxalyl chloride, Et₃N / CH₂Cl₂; dimethylsulfoxide

7: Jones reagent / acetone

8: diethyl ether

With 1H-imidazole; jones reagent; oxalyl dichloride; acetic acid; triethylamine; benzenesulfonic acid; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0008-6215(00)90828-0