6-O-allyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

Base Information

• Chemical Name: 6-O-allyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose
• CAS No.: 246162-52-7
• Molecular Formula: C₂₆H₃₂O₆
• Molecular Weight: 440.536
• Mol file: 246162-52-7.mol

Synonyms:6-O-allyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

Chemical Property of 6-O-allyl-3,5-di-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-allyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

There total 2 articles about 6-O-allyl-3,5-di-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: 96.0%

benzyl bromide (100-39-0) + 6-O-allyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (82185-84-0) → 6-O-allyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (246162-52-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 5h;

DOI:10.1080/07328309908544035

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-allyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (246162-52-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / Bu₄NBr; NaOH / CH₂Cl₂ / 2 h / 20 °C

2: 96 percent / NaH / dimethylformamide / 5 h / 20 °C

With sodium hydroxide; tetrabutylammomium bromide; sodium hydride; In dichloromethane; N,N-dimethyl-formamide; 1: Alkylation / 2: Substitution;

DOI:10.1080/07328309908544035

Reference yield: 89.0%

6-O-allyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (246162-52-7) → 6-O-allyl-3,5-di-O-benzyl-D-glucofuranose

Guidance literature:

With sulfuric acid; In 1,4-dioxane; for 2h; Heating;

DOI:10.1080/07328309908544035

upstream raw materials:

benzyl bromide

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

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

Downstream raw materials:

3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose