5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-β-D-threo-pentofuranose-3-ulose

Base Information

• Chemical Name: 5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-β-D-threo-pentofuranose-3-ulose
• CAS No.: 172751-32-5
• Molecular Formula: C₂₄H₃₀O₅Si
• Molecular Weight: 426.585
• Mol file: 172751-32-5.mol

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

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

There total 8 articles about 5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-β-D-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%

(3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (114738-04-4) → 5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-β-D-threo-pentofuranose-3-ulose (172751-32-5)

Guidance literature:

With pyridine; chromium(VI) oxide; acetic anhydride; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1021/jo010299j

Reference yield:

D-arabinose diethyl dithioacetal (1941-50-0) → 5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-β-D-threo-pentofuranose-3-ulose (172751-32-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 94 percent / imidazole / dimethylformamide / 0 °C

2.1: HgO; HgCl₂ / acetone

2.2: 84 percent / CuSO₄; H⁽¹⁺⁾ / acetone

3.1: (COCl)2; DMSO; TEA / CH₂Cl₂ / -78 - -35 °C

With 1H-imidazole; oxalyl dichloride; TEA; dimethyl sulfoxide; mercury dichloride; mercury(II) oxide; In dichloromethane; N,N-dimethyl-formamide; acetone; 3.1: Swern oxidation;

DOI:10.1016/S0040-4039(01)00376-8

Reference yield:

5-O-(tert-butyldiphenylsilyl)-D-arabinose diethyldithioacetal (162517-90-0) → 5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-β-D-threo-pentofuranose-3-ulose (172751-32-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: HgO; HgCl₂ / acetone

1.2: 84 percent / CuSO₄; H⁽¹⁺⁾ / acetone

2.1: (COCl)2; DMSO; TEA / CH₂Cl₂ / -78 - -35 °C

With oxalyl dichloride; TEA; dimethyl sulfoxide; mercury dichloride; mercury(II) oxide; In dichloromethane; acetone; 2.1: Swern oxidation;

DOI:10.1016/S0040-4039(01)00376-8

upstream raw materials:

(3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

D-Arabinose

D-arabinose diethyl dithioacetal

5-O-(tert-butyldiphenylsilyl)-D-arabinose diethyldithioacetal

Downstream raw materials:

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

5-O-(tert-butyldiphenylsilyl)-3-C-(3-hydroxypropyl)-1,2-O-isopropylidene-β-D-lyxofuranose

C₂₄H₃₁⁽²⁾HO₅Si

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