3-O-benzyl-5-O-[tert-butyl(dimethyl)silyl]-4-(hydroxymethyl)-1,2-O-(1-methylethylidene)-β-L-arabinofuranose

Base Information

• Chemical Name: 3-O-benzyl-5-O-[tert-butyl(dimethyl)silyl]-4-(hydroxymethyl)-1,2-O-(1-methylethylidene)-β-L-arabinofuranose
• CAS No.: 1027758-99-1
• Molecular Formula: C₂₂H₃₆O₆Si
• Molecular Weight: 424.61
• Mol file: 1027758-99-1.mol

Synonyms:3-O-benzyl-5-O-[tert-butyl(dimethyl)silyl]-4-(hydroxymethyl)-1,2-O-(1-methylethylidene)-β-L-arabinofuranose

Chemical Property of 3-O-benzyl-5-O-[tert-butyl(dimethyl)silyl]-4-(hydroxymethyl)-1,2-O-(1-methylethylidene)-β-L-arabinofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzyl-5-O-[tert-butyl(dimethyl)silyl]-4-(hydroxymethyl)-1,2-O-(1-methylethylidene)-β-L-arabinofuranose

There total 3 articles about 3-O-benzyl-5-O-[tert-butyl(dimethyl)silyl]-4-(hydroxymethyl)-1,2-O-(1-methylethylidene)-β-L-arabinofuranose 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: 59.0%

1,2-O-isopropylidene-3-O-benzyl-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose (72261-44-0) + tert-butyldimethylsilyl chloride (18162-48-6) → 3-O-benzyl-5-O-[tert-butyl(dimethyl)silyl]-4-(hydroxymethyl)-1,2-O-(1-methylethylidene)-β-L-arabinofuranose (1027758-99-1)

Guidance literature:

With 1H-imidazole; In dichloromethane; at -20 ℃; for 1h;

DOI:10.1021/jo8002826

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → 3-O-benzyl-5-O-[tert-butyl(dimethyl)silyl]-4-(hydroxymethyl)-1,2-O-(1-methylethylidene)-β-L-arabinofuranose (1027758-99-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / 1,4-dioxane

2: 1H-imidazole / dichloromethane / -20 °C

With 1H-imidazole; sodium hydroxide; In 1,4-dioxane; dichloromethane;

Reference yield:

1-2,5-6 di-O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose (591727-19-4) → 3-O-benzyl-5-O-[tert-butyl(dimethyl)silyl]-4-(hydroxymethyl)-1,2-O-(1-methylethylidene)-β-L-arabinofuranose (1027758-99-1)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid; water

2: sodium hydroxide / 1,4-dioxane

3: 1H-imidazole / dichloromethane / -20 °C

With 1H-imidazole; water; acetic acid; sodium hydroxide; In 1,4-dioxane; dichloromethane;

upstream raw materials:

1,2-O-isopropylidene-3-O-benzyl-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose

tert-butyldimethylsilyl chloride

1-2,5-6 di-O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

Downstream raw materials:

C₂₂H₃₄O₆Si

C₂₅H₄₀O₆Si

C₃₀H₄₈O₇Si

C₂₄H₃₄O₇