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

Base Information

Chemical Name:6-O-acetyl-3-O-benzyl-5-O-(β-hydroxyethyl)-1,2-O-isopropylidene-α-D-glucofuranose
CAS No.:263916-90-1
Molecular Formula:C₂₀H₂₈O₈
Molecular Weight:396.438
Hs Code.:

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

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

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

There total 3 articles about 6-O-acetyl-3-O-benzyl-5-O-(β-hydroxyethyl)-1,2-O-isopropylidene-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: 81.0%

: 263916-89-8
6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-5-O-(prop-2'-enyl)-α-D-glucofuranose

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

Guidance literature:: 6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-5-O-(prop-2'-enyl)-α-D-glucofuranose; With ozone; In methanol; dichloromethane; at -78 ℃; for 0.5h;

With sodium tetrahydroborate; In methanol; dichloromethane; at -78 - 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

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

Guidance literature:: Multi-step reaction with 3 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

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;
DOI:10.1080/07328300008544068

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 2 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

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