(-)-<2S(2α,5α)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane-5-methanol

Base Information

• Chemical Name: (-)-<2S(2α,5α)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane-5-methanol
• CAS No.: 140436-34-6
• Molecular Formula: C₂₁H₂₈O₃SSi
• Molecular Weight: 388.603
• Mol file: 140436-34-6.mol

Synonyms:(-)-<2S(2α,5α)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane-5-methanol

Chemical Property of (-)-<2S(2α,5α)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane-5-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-<2S(2α,5α)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane-5-methanol

There total 2 articles about (-)-<2S(2α,5α)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane-5-methanol 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%

(-)-<2S(2α,5α)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane-5-methanol 5-benzoate (140436-33-5) → (-)-<2S(2α,5α)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane-5-methanol (140436-34-6)

Guidance literature:

With sodium methylate; In methanol; for 2h; Ambient temperature;

DOI:10.1021/jm00070a006

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (-)-<2S(2α,5α)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane-5-methanol (140436-34-6)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / Ambient temperature

2: NaOMe / methanol / Ambient temperature

With 1H-imidazole; sodium methylate; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)92319-0

Reference yield:

(-)-<2S(2α,5α)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane-5-methanol (140436-34-6) → <2S(2α,5α)>- and <2S(2α,5β)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-ol acetate (202532-88-5)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridinium dichromate (PDC) / dimethylformamide / 15 h / Ambient temperature

2: pyridine / ethyl acetate / 2 h / Ambient temperature

With pyridine; dipyridinium dichromate; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00070a006

upstream raw materials:

(-)-<2S(2α,5α)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane-5-methanol 5-benzoate

tert-butylchlorodiphenylsilane

Downstream raw materials:

<2S(2α,5α)>- and <2S(2α,5β)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-ol acetate

(-)-(2S,5S)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-cystosine

(+)-(2S,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-cystosine

(-)-(2S,5S)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N₄-acetylcystosine