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

Base Information

Chemical Name:(-)-<2S,<2α,5α(R)>>-2-benzoyl-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-1,2-ethanediol
CAS No.:149712-84-5
Molecular Formula:C₂₉H₃₄O₅SSi
Molecular Weight:522.737
Hs Code.:

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

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

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

There total 4 articles about (-)-<2S,<2α,5α(R)>>-2-benzoyl-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: 91.0%

: 136794-43-9
(-)-<2S,<2α,5α(R)>>-2-benzoyl-1-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>-1,2-ethanediol

: 58479-61-1
tert-butylchlorodiphenylsilane

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

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; Ambient temperature;
DOI:10.1021/jm00070a006

Reference yield:

: 136794-41-7
(-)-4-O-benzoyl-1,6-dideoxy-1,6-thioanhydro-D-mannopyranose

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

Guidance literature:: Multi-step reaction with 3 steps

1: Pb(OAc)4 / ethyl acetate / 0.08 h / 0 °C

2: NaBH₄ / ethanol

3: 91 percent / imidazole / dimethylformamide / Ambient temperature

With 1H-imidazole; lead(IV) acetate; sodium tetrahydroborate; In ethanol; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jm00070a006

Reference yield:

: 136794-40-6
(-)-4-O-benzoyl-2,3-O-isopropylidene-1,6-dideoxy-1,6-thioanhydro-D-mannopyranose

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

Guidance literature:: Multi-step reaction with 4 steps

1: 85 percent / aq. H₂SO₄ / dioxane / 5 h / 70 °C

2: Pb(OAc)4 / ethyl acetate / 0.08 h / 0 °C

3: NaBH₄ / ethanol

4: 91 percent / imidazole / dimethylformamide / Ambient temperature

With 1H-imidazole; lead(IV) acetate; sodium tetrahydroborate; sulfuric acid; In 1,4-dioxane; ethanol; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jm00070a006