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

Base Information

• Chemical Name: <2S(2α,5α)>- and <2S(2α,5β)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-ol acetate
• CAS No.: 202532-88-5
• Molecular Formula: C₂₂H₂₈O₄SSi
• Molecular Weight: 416.613
• Mol file: 202532-88-5.mol

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

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

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about <2S(2α,5α)>- and <2S(2α,5β)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-ol acetate 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:

lead(IV) tetraacetate (546-67-8) + (-)-<2S(2α,5α)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane-5-carboxylic acid (140630-83-7) → <2S(2α,5α)>- and <2S(2α,5β)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-ol acetate (202532-88-5)

Guidance literature:

With pyridine; In ethyl acetate;

DOI:10.1021/jo00023a010

Reference yield:

(2S,5S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]oxathiolane-5-carbaldehyde (148774-90-7) → <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 5 steps

1: aq. NaH₂PO₄*H₂O, 2-methyl-2-butene, aq. NaClO₂ / acetonitrile / 3 h / Ambient temperature

2: K₂CO₃ / acetone

3: 80 percent / BHCl₂*(CH₃)2S / tetrahydrofuran / 1.75 h / 5 - 20 °C

4: LiOH / tetrahydrofuran; H₂O / Ambient temperature

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

With pyridine; lithium hydroxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; dichloroborane-dimethyl sulfide; potassium carbonate; In tetrahydrofuran; water; ethyl acetate; acetone; acetonitrile;

DOI:10.1021/jm00070a006

Reference yield:

<2S,(2α,3β,5α)>- and <2S(2α,3α,5α)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane-5-carboxylic acid methyl ester 3-oxide (136794-46-2,136846-22-5) → <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 3 steps

1: 80 percent / BHCl₂*(CH₃)2S / tetrahydrofuran / 1.75 h / 5 - 20 °C

2: LiOH / tetrahydrofuran; H₂O / Ambient temperature

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

With pyridine; lithium hydroxide; dichloroborane-dimethyl sulfide; In tetrahydrofuran; water; ethyl acetate;

DOI:10.1021/jm00070a006

upstream raw materials:

lead(IV) tetraacetate

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

(2S,5S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]oxathiolane-5-carbaldehyde

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

Downstream raw materials:

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

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

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

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