5-O-tert-butyldiphenylsilyl-1,2-O-(1-methylethylidene)-β-L-threo-pentofuranose-3-ulose

Base Information

• Chemical Name: 5-O-tert-butyldiphenylsilyl-1,2-O-(1-methylethylidene)-β-L-threo-pentofuranose-3-ulose
• CAS No.: 103763-15-1
• Molecular Formula: C₂₄H₃₀O₅Si
• Molecular Weight: 426.585
• Mol file: 103763-15-1.mol

Synonyms:5-O-tert-butyldiphenylsilyl-1,2-O-(1-methylethylidene)-β-L-threo-pentofuranose-3-ulose

Chemical Property of 5-O-tert-butyldiphenylsilyl-1,2-O-(1-methylethylidene)-β-L-threo-pentofuranose-3-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-tert-butyldiphenylsilyl-1,2-O-(1-methylethylidene)-β-L-threo-pentofuranose-3-ulose

There total 6 articles about 5-O-tert-butyldiphenylsilyl-1,2-O-(1-methylethylidene)-β-L-threo-pentofuranose-3-ulose 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: 90.0%

(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) → 5-O-tert-butyldiphenylsilyl-1,2-O-(1-methylethylidene)-β-L-threo-pentofuranose-3-ulose (103763-15-1)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.carres.2007.10.035

Reference yield: 73.0%

L-arabinose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) + 2,2-dimethoxy-propane (77-76-9) + tert-butylchlorodiphenylsilane (58479-61-1) → 5-O-tert-butyldiphenylsilyl-1,2-O-(1-methylethylidene)-β-L-threo-pentofuranose-3-ulose (103763-15-1)

Guidance literature:

L-arabinose; tert-butylchlorodiphenylsilane; With 1H-imidazole; In N,N-dimethyl-formamide; at 65 ℃; Inert atmosphere;

2,2-dimethoxy-propane; With iodine; In acetone; at 20 ℃; Inert atmosphere;

With Dess-Martin periodane; In dichloromethane; at 20 ℃;

DOI:10.1039/c9cc09093b

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 5-O-tert-butyldiphenylsilyl-1,2-O-(1-methylethylidene)-β-L-threo-pentofuranose-3-ulose (103763-15-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) imidazole, 2.) sulfuric acid, copper(II) sulfate / 1.) DMF, 60 deg C, 2 h, 2.) room temperature, 17 h

2: 84 percent / Chromium(VI) oxide, pyridine / CH₂Cl₂; acetic anhydride / 0.17 h / Ambient temperature

With pyridine; 1H-imidazole; chromium(VI) oxide; sulfuric acid; copper(II) sulfate; In dichloromethane; acetic anhydride;

upstream raw materials:

(3aR,5S,6S,6aR)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol

D-Arabinose

tert-butylchlorodiphenylsilane

L-arabinose

Downstream raw materials:

(3aR,5S,6R,6aR)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-6-trimethylsilanylmethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol

5-t-butyldiphenylsilyloxymethyl-6-(2-furyl)-2,2-dimethyl-(3aR,5S,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-ol

5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-β-L-lyxofuranose

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