5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-3-O-(phenoxythiocarbonyl)-β-L-arabinofuranose

Base Information

• Chemical Name: 5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-3-O-(phenoxythiocarbonyl)-β-L-arabinofuranose
• CAS No.: 150943-34-3
• Molecular Formula: C₃₁H₃₆O₆SSi
• Molecular Weight: 564.775
• Mol file: 150943-34-3.mol

Synonyms:5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-3-O-(phenoxythiocarbonyl)-β-L-arabinofuranose

Chemical Property of 5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-3-O-(phenoxythiocarbonyl)-β-L-arabinofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-3-O-(phenoxythiocarbonyl)-β-L-arabinofuranose

There total 7 articles about 5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-3-O-(phenoxythiocarbonyl)-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: 94.0%

5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-L-xylofuranose (220827-73-6) + phenylcarbonochloridothioate (1005-56-7) → Thiocarbonic acid O-[(3aS,5S,6R,6aS)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester O-phenyl ester (114861-15-3,150943-34-3)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 0 - 25 ℃; for 15h;

DOI:10.1021/ja00241a062

Reference yield: 67.0%

(3aR,5S,6S,6aR)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol (103763-14-0) + phenylcarbonochloridothioate (1005-56-7) → 5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-3-O-(phenoxythiocarbonyl)-β-L-arabinofuranose (150943-34-3)

Guidance literature:

With dmap; In acetonitrile; for 18h; Ambient temperature;

DOI:10.1021/jm00035a018

Reference yield:

1,2-O-isopropylidene-α-L-xylofuranose (114861-22-2) → Thiocarbonic acid O-[(3aS,5S,6R,6aS)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester O-phenyl ester (114861-15-3,150943-34-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

2: 94 percent / pyridine / DMAP / CH₂Cl₂ / 15 h / 0 - 25 °C

With pyridine; 1H-imidazole; dmap; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00222a028

upstream raw materials:

5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-L-xylofuranose

phenylcarbonochloridothioate

tert-butylchlorodiphenylsilane

1,2-O-isopropylidene-α-L-xylofuranose

Downstream raw materials:

(R)-1-O-(tert-butyldiphenylsilyl)-4-chloro-1,2-butanediol

(R)-1-O-(tert-butyldiphenylsilyl)-1,2,4-butanetriol

(R)-1-((tert-butyldiphenylsilyl)oxy)-4-chloro-2-(methoxymethoxy)butane

5-O-(tert-butyldiphenylsilyl)-3-deoxy-1,2-O-isopropylidene-β-L-treopentofuranose