3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-[2'-O-acetyl-4'-O-benzyl-3-(2'',3'',4''-tri-O-benzyl-α-L-rhamnopyranosyl)]-β-L-rhamnopyranosyl thiol

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Chemical Name:3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-[2'-O-acetyl-4'-O-benzyl-3-(2'',3'',4''-tri-O-benzyl-α-L-rhamnopyranosyl)]-β-L-rhamnopyranosyl thiol
CAS No.:1309779-46-1
Molecular Formula:C₅₄H₆₈O₁₅S
Molecular Weight:989.191
Hs Code.:

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Chemical Property of 3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-[2'-O-acetyl-4'-O-benzyl-3-(2'',3'',4''-tri-O-benzyl-α-L-rhamnopyranosyl)]-β-L-rhamnopyranosyl thiol

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Technology Process of 3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-[2'-O-acetyl-4'-O-benzyl-3-(2'',3'',4''-tri-O-benzyl-α-L-rhamnopyranosyl)]-β-L-rhamnopyranosyl thiol

There total 13 articles about 3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-[2'-O-acetyl-4'-O-benzyl-3-(2'',3'',4''-tri-O-benzyl-α-L-rhamnopyranosyl)]-β-L-rhamnopyranosyl thiol 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: 99.0%

: 1309779-44-9
5-nitro-2-pyridyl 3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-[2',-O-acetyl-4',-O-benzyl-3-(2'',3'',4''-tri-O-benzyl-α-L-rhamnopyranosyl)]-β-L-rhamnopyranosyl disulfide

: 2127-09-5
2-mercapto-5-nitropyridine

: 1309779-46-1
3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-[2'-O-acetyl-4'-O-benzyl-3-(2'',3'',4''-tri-O-benzyl-α-L-rhamnopyranosyl)]-β-L-rhamnopyranosyl thiol

Guidance literature:: With tributylphosphine; In 1,4-dioxane; chloroform; water; Inert atmosphere;
DOI:10.1002/anie.201006327

Reference yield:

: 1309779-36-9
3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-triethylsilyl-α-L-rhamnopyranosyl bromide

: 1309779-46-1
3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-[2'-O-acetyl-4'-O-benzyl-3-(2'',3'',4''-tri-O-benzyl-α-L-rhamnopyranosyl)]-β-L-rhamnopyranosyl thiol

Guidance literature:: Multi-step reaction with 5 steps

1.1: tetrabutylammomium bromide / 1,4-dioxane / 16 h / 73 °C / Molecular sieve

2.1: triethylamine / dichloromethane / 0 - 20 °C

3.1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 20 h / Inert atmosphere

4.1: N-(phenylthio)-ε-caprolactam; 2,4,6-tri-tertbutylpyridine / dichloromethane / 1 h / Inert atmosphere; Molecular sieve

4.2: 1 h / 10 °C / Inert atmosphere

5.1: tributylphosphine / 1,4-dioxane; chloroform; water / Inert atmosphere

With N-(phenylthio)-ε-caprolactam; 2,4,6-tri-tertbutylpyridine; tributylphosphine; tetrabutylammomium bromide; triethylamine tris(hydrogen fluoride); triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; chloroform; water;
DOI:10.1002/anie.201006327

Reference yield:

: 1309779-37-0
3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-triethylsilyl-L-rhamnopyranosyl methanethiosulfonate

: 1309779-46-1
3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-[2'-O-acetyl-4'-O-benzyl-3-(2'',3'',4''-tri-O-benzyl-α-L-rhamnopyranosyl)]-β-L-rhamnopyranosyl thiol

Guidance literature:: Multi-step reaction with 4 steps

1.1: triethylamine / dichloromethane / 0 - 20 °C

2.1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 20 h / Inert atmosphere

3.1: N-(phenylthio)-ε-caprolactam; 2,4,6-tri-tertbutylpyridine / dichloromethane / 1 h / Inert atmosphere; Molecular sieve

3.2: 1 h / 10 °C / Inert atmosphere

4.1: tributylphosphine / 1,4-dioxane; chloroform; water / Inert atmosphere

With N-(phenylthio)-ε-caprolactam; 2,4,6-tri-tertbutylpyridine; tributylphosphine; triethylamine tris(hydrogen fluoride); triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; chloroform; water;
DOI:10.1002/anie.201006327