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

Base Information

Chemical Name: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
CAS No.:1309779-44-9
Molecular Formula:C₅₉H₇₀N₂O₁₇S₂
Molecular Weight:1143.34
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 11 articles about 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 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: 66.0%

: 1309779-40-5
5-nitro-2-pyridyl 3,4-O-(2,3-dimethoxybutane-2,3-diyl)-α-L-rhamnopyranosyl disulfide

: 1309779-43-8
ethyl 2-O-acetyl-4-O-benzyl-3-(2',3',4'-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl disulfide

: 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

Guidance literature:: 5-nitro-2-pyridyl 3,4-O-(2,3-dimethoxybutane-2,3-diyl)-α-L-rhamnopyranosyl disulfide; ethyl 2-O-acetyl-4-O-benzyl-3-(2',3',4'-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl disulfide; With N-(phenylthio)-ε-caprolactam; 2,4,6-tri-tertbutylpyridine; In dichloromethane; for 1h; Inert atmosphere; Molecular sieve;

With trifluoromethylsulfonic anhydride; In dichloromethane; at 10 ℃; for 1h; diastereoselective reaction; 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

: 1309779-44-9
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

Guidance literature:: Multi-step reaction with 4 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

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

: 1309779-44-9
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

Guidance literature:: Multi-step reaction with 3 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

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