6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

Base Information

• Chemical Name: 6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose
• CAS No.: 177897-25-5
• Molecular Formula: C₁₈H₂₄O₇
• Molecular Weight: 352.384
• Mol file: 177897-25-5.mol

Synonyms:6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

Chemical Property of 6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

There total 5 articles about 6-O-acetyl-3-O-benzyl-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: 62.0%

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) + acetyl chloride (75-36-5) → 6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (177897-25-5)

Guidance literature:

In pyridine; dichloromethane; at -78 ℃; for 1h;

DOI:10.1080/07328300008544068

Reference yield:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) + acetic anhydride (108-24-7) → 6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (177897-25-5)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 2h; regioselective reaction; Inert atmosphere;

DOI:10.1039/c1ob06415k

Reference yield:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) → 6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (177897-25-5)

Guidance literature:

Multi-step reaction with 3 steps

1: diisopropylethylamine / CH₂Cl₂ / 32 h

2: diisopropylethylamine, dimethylaminopyridine / CH₂Cl₂ / 0.5 h

3: tetra-O-butylammonium fluoride / CH₂Cl₂ / Ambient temperature

With dmap; tetra-O-butylammonium fluoride; N-ethyl-N,N-diisopropylamine; In dichloromethane;

upstream raw materials:

Acetic acid (R)-1-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester

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

acetyl chloride

1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethanol

Downstream raw materials:

6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-5-O-methanesulfonyl-α-D-glucofuranose

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

Toluene-4-sulfonic acid 2-[(R)-2-hydroxy-1-((3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-ethyl ester

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