ethyl 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

Base Information

• Chemical Name: ethyl 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
• CAS No.: 1309779-47-2
• Molecular Formula: C₅₆H₇₂O₁₅S₂
• Molecular Weight: 1049.31

Synonyms:

Chemical Property of ethyl 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 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

There total 15 articles about ethyl 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 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: 78.0%

S-ethyl methanethiosulfonate (2043-76-7) + 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 (1309779-46-1) → ethyl 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 (1309779-47-2)

Guidance literature:

With triethylamine; In dichloromethane; for 1.5h; Cooling with ice;

DOI:10.1002/anie.201006327

Reference yield:

ethyl 1-thio-α-L-rhamnopyranoside (127753-94-0) → ethyl 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 (1309779-47-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: camphor-10-sulfonic acid; dimethylglyoxal / methanol / 16 h / Reflux

2.1: pyridine / dichloromethane / 0 - 20 °C

3.1: bromine / dichloromethane / 0.5 h / 0 °C / Molecular sieve

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

5.1: triethylamine / dichloromethane / 0 - 20 °C

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

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

7.2: 1 h / 10 °C / Inert atmosphere

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

9.1: triethylamine / dichloromethane / 1.5 h / Cooling with ice

With pyridine; N-(phenylthio)-ε-caprolactam; 2,4,6-tri-tertbutylpyridine; tributylphosphine; camphor-10-sulfonic acid; tetrabutylammomium bromide; bromine; triethylamine tris(hydrogen fluoride); triethylamine; dimethylglyoxal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; water;

DOI:10.1002/anie.201006327

Reference yield:

ethyl 3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-triethylsilyl-α-Lthiorhamnopyranoside (1309779-35-8) → ethyl 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 (1309779-47-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: bromine / dichloromethane / 0.5 h / 0 °C / Molecular sieve

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

3.1: triethylamine / dichloromethane / 0 - 20 °C

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

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

5.2: 1 h / 10 °C / Inert atmosphere

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

7.1: triethylamine / dichloromethane / 1.5 h / Cooling with ice

With N-(phenylthio)-ε-caprolactam; 2,4,6-tri-tertbutylpyridine; tributylphosphine; tetrabutylammomium bromide; bromine; triethylamine tris(hydrogen fluoride); triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; chloroform; water;

DOI:10.1002/anie.201006327

upstream raw materials:

5-nitro-2-pyridyl 2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl disulfide

ethyl 3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-triethylsilyl-α-Lthiorhamnopyranoside

3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-triethylsilyl-α-L-rhamnopyranosyl bromide

3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-triethylsilyl-L-rhamnopyranosyl methanethiosulfonate

Downstream raw materials:

C₈₀H₁₁₂O₂₇S₂

C₈₃H₁₁₀N₂O₂₉S₂

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