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

Base Information

• Chemical Name: (-)-<2S,<2α(R),5α>>-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-1,2-ethanediol
• CAS No.: 136794-44-0
• Molecular Formula: C₂₂H₃₀O₄SSi
• Molecular Weight: 418.629

Synonyms:(-)-<2S,<2α(R),5α>>-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-1,2-ethanediol

Chemical Property of (-)-<2S,<2α(R),5α>>-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-1,2-ethanediol

Chemical Property:

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Technology Process of (-)-<2S,<2α(R),5α>>-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-1,2-ethanediol

There total 11 articles about (-)-<2S,<2α(R),5α>>-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-1,2-ethanediol 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: 93.0%

(-)-<2S,<2α,5α(R)>>-2-benzoyl-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-1,2-ethanediol (149712-84-5) → (-)-<2S,<2α(R),5α>>-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-1,2-ethanediol (136794-44-0)

Guidance literature:

With ammonium hydroxide; In methanol; for 12h; Ambient temperature;

DOI:10.1021/jm00070a006

Reference yield:

(-)-<2S,<2α,5α(R)>>-2-benzoyl-1-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>-1,2-ethanediol (136794-43-9) → (-)-<2S,<2α(R),5α>>-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-1,2-ethanediol (136794-44-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / imidazole / dimethylformamide / Ambient temperature

2: 93 percent / conc. NH₄OH / methanol / 12 h / Ambient temperature

With 1H-imidazole; ammonium hydroxide; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00070a006

Reference yield:

tert-Butyl-[(2R,5R)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-[1,3]oxathiolan-2-ylmethoxy]-diphenyl-silane → 1-[(2R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]oxathiolan-5-yl]-ethane-1,2-diol (136794-44-0,139757-71-4,148812-30-0)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; Yield given; Ambient temperature;

DOI:10.1021/jo00034a006

upstream raw materials:

(-)-<2S,<2α,5α(R)>>-2-benzoyl-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-1,2-ethanediol

(-)-<2S,<2α,5α(R)>>-2-benzoyl-1-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>-1,2-ethanediol

L-gulose

[(2R,5R)-5-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-[1,3]oxathiolan-2-yl]-methanol

Downstream raw materials:

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

(2R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]oxathiolane-5-carboxylic acid

(+)-(2R,5RS)-5-acetoxy-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane

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

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