3'-O-acetyl-5,2',4',6'-tetra-O-benzyl-3-O-(α-D-glucopyranosyl)-1,2-O-isopropylidene-α-D-ribofuranoside

Base Information

Chemical Name:3'-O-acetyl-5,2',4',6'-tetra-O-benzyl-3-O-(α-D-glucopyranosyl)-1,2-O-isopropylidene-α-D-ribofuranoside
CAS No.:1357153-85-5
Molecular Formula:C₄₄H₅₀O₁₁
Molecular Weight:754.874
Hs Code.:

Synonyms:3'-O-acetyl-5,2',4',6'-tetra-O-benzyl-3-O-(α-D-glucopyranosyl)-1,2-O-isopropylidene-α-D-ribofuranoside

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Chemical Property of 3'-O-acetyl-5,2',4',6'-tetra-O-benzyl-3-O-(α-D-glucopyranosyl)-1,2-O-isopropylidene-α-D-ribofuranoside

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Technology Process of 3'-O-acetyl-5,2',4',6'-tetra-O-benzyl-3-O-(α-D-glucopyranosyl)-1,2-O-isopropylidene-α-D-ribofuranoside

There total 5 articles about 3'-O-acetyl-5,2',4',6'-tetra-O-benzyl-3-O-(α-D-glucopyranosyl)-1,2-O-isopropylidene-α-D-ribofuranoside 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: 76.0%

: 2592-42-9,23202-83-7
5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose

: ethyl 3-O-acetyl-2,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

: 1357153-85-5
3'-O-acetyl-5,2',4',6'-tetra-O-benzyl-3-O-(α-D-glucopyranosyl)-1,2-O-isopropylidene-α-D-ribofuranoside

Guidance literature:: 5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose; ethyl 3-O-acetyl-2,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside; In 1,4-dioxane; toluene; for 0.25h; Inert atmosphere; Molecular sieve;

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In 1,4-dioxane; toluene; at 20 ℃; for 0.5h; Inert atmosphere; Molecular sieve;
DOI:10.1021/jm201571p

Reference yield:

: 1357153-84-4
ethyl 4,6-di-O-benzyl-1-thio-β-D-glucopyranoside

: 1357153-85-5
3'-O-acetyl-5,2',4',6'-tetra-O-benzyl-3-O-(α-D-glucopyranosyl)-1,2-O-isopropylidene-α-D-ribofuranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrabutylammomium bromide; di(n-butyl)tin oxide / acetonitrile / 24 h / Inert atmosphere; Reflux; Molecular sieve

2.1: pyridine / 12 h / 20 °C / Inert atmosphere

3.1: 1,4-dioxane; toluene / 0.25 h / Inert atmosphere; Molecular sieve

3.2: 0.5 h / 20 °C / Inert atmosphere; Molecular sieve

With pyridine; tetrabutylammomium bromide; di(n-butyl)tin oxide; In 1,4-dioxane; toluene; acetonitrile;
DOI:10.1021/jm201571p

Reference yield:

: 100-39-0
benzyl bromide

: 1357153-85-5
3'-O-acetyl-5,2',4',6'-tetra-O-benzyl-3-O-(α-D-glucopyranosyl)-1,2-O-isopropylidene-α-D-ribofuranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: acetic acid / water / 1 h / Inert atmosphere; Reflux

3.1: tetrabutylammomium bromide; di(n-butyl)tin oxide / acetonitrile / 24 h / Inert atmosphere; Reflux; Molecular sieve

4.1: pyridine / 12 h / 20 °C / Inert atmosphere

5.1: 1,4-dioxane; toluene / 0.25 h / Inert atmosphere; Molecular sieve

5.2: 0.5 h / 20 °C / Inert atmosphere; Molecular sieve

With pyridine; tetrabutylammomium bromide; sodium hydride; di(n-butyl)tin oxide; acetic acid; In 1,4-dioxane; water; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil;
DOI:10.1021/jm201571p