6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-5-O-(β-p-toluenesulfonyloxyethyl)-α-D-glucofuranose

Base Information

Chemical Name:6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-5-O-(β-p-toluenesulfonyloxyethyl)-α-D-glucofuranose
CAS No.:263916-91-2
Molecular Formula:C₂₇H₃₄O₁₀S
Molecular Weight:550.627
Hs Code.:

Synonyms:6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-5-O-(β-p-toluenesulfonyloxyethyl)-α-D-glucofuranose

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Chemical Property of 6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-5-O-(β-p-toluenesulfonyloxyethyl)-α-D-glucofuranose

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Technology Process of 6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-5-O-(β-p-toluenesulfonyloxyethyl)-α-D-glucofuranose

There total 4 articles about 6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-5-O-(β-p-toluenesulfonyloxyethyl)-α-D-glucofuranose 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: 70.0%

: 98-59-9
p-toluenesulfonyl chloride

: 263916-90-1
6-O-acetyl-3-O-benzyl-5-O-(β-hydroxyethyl)-1,2-O-isopropylidene-α-D-glucofuranose

: 263916-91-2
6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-5-O-(β-p-toluenesulfonyloxyethyl)-α-D-glucofuranose

Guidance literature:: In pyridine; dichloromethane; at 20 ℃;
DOI:10.1080/07328300008544068

Reference yield:

: 22529-61-9
(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

: 263916-91-2
6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-5-O-(β-p-toluenesulfonyloxyethyl)-α-D-glucofuranose

Guidance literature:: Multi-step reaction with 4 steps

1.1: 62 percent / CH₂Cl₂; pyridine / 1 h / -78 °C

2.1: 82 percent / tris(dibenzylideneacetone)dipalladium; 1,4-bis-(diphenylphosphino)butane / tetrahydrofuran / 60 °C

3.1: O₃ / CH₂Cl₂; methanol / 0.5 h / -78 °C

3.2: 81 percent / NaBH₄ / CH₂Cl₂; methanol / -78 - 20 °C

4.1: 70 percent / CH₂Cl₂; pyridine / 20 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; ozone; 1,4-di(diphenylphosphino)-butane; In tetrahydrofuran; pyridine; methanol; dichloromethane; 1.1: Acetylation / 2.1: Alkylation / 3.1: Oxidation / 3.2: Reduction / 4.1: Tosylation;
DOI:10.1080/07328300008544068

Reference yield:

: 177897-25-5
6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

: 263916-91-2
6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-5-O-(β-p-toluenesulfonyloxyethyl)-α-D-glucofuranose

Guidance literature:: Multi-step reaction with 3 steps

1.1: 82 percent / tris(dibenzylideneacetone)dipalladium; 1,4-bis-(diphenylphosphino)butane / tetrahydrofuran / 60 °C

2.1: O₃ / CH₂Cl₂; methanol / 0.5 h / -78 °C

2.2: 81 percent / NaBH₄ / CH₂Cl₂; methanol / -78 - 20 °C

3.1: 70 percent / CH₂Cl₂; pyridine / 20 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; ozone; 1,4-di(diphenylphosphino)-butane; In tetrahydrofuran; pyridine; methanol; dichloromethane; 1.1: Alkylation / 2.1: Oxidation / 2.2: Reduction / 3.1: Tosylation;
DOI:10.1080/07328300008544068