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

Base Information

• Chemical Name: (-)-<2S(2α,5α)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane-5-methanol 5-benzoate
• CAS No.: 140436-33-5
• Molecular Formula: C₂₈H₃₂O₄SSi
• Molecular Weight: 492.711
• Mol file: 140436-33-5.mol

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

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

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 5-benzoate

There total 9 articles about (-)-<2S(2α,5α)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane-5-methanol 5-benzoate 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: 98.0%

(-)-<2S(2α,5α)>-1,3-oxathiolane-2,5-dimethanol 5-benzoate (140436-32-4) + tert-butylchlorodiphenylsilane (58479-61-1) → (-)-<2S(2α,5α)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane-5-methanol 5-benzoate (140436-33-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 1h; Ambient temperature;

DOI:10.1021/jm00070a006

Reference yield:

benzoyl chloride (98-88-4) → (-)-<2S(2α,5α)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane-5-methanol 5-benzoate (140436-33-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / pyridine / 1 h / Ambient temperature

2: p-toluenesulfonic acid / methanol / 7 h / Ambient temperature

3: aq. NaIO₄ / methanol / 0.17 h

4: NaBH₄ / methanol / 0.08 h

5: 98 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium periodate; toluene-4-sulfonic acid; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00070a006

Reference yield:

Benzoic acid (2S,5S)-2-formyl-[1,3]oxathiolan-5-ylmethyl ester → (-)-<2S(2α,5α)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane-5-methanol 5-benzoate (140436-33-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄ / methanol / 0.08 h

2: 98 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

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

DOI:10.1021/jm00070a006

upstream raw materials:

(-)-<2S(2α,5α)>-1,3-oxathiolane-2,5-dimethanol 5-benzoate

tert-butylchlorodiphenylsilane

benzoyl chloride

(-)-<2S<2α(S),5α>>-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-1,3-oxathiolane-5-methanol

Downstream raw materials:

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

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

<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