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

Base Information

• Chemical Name: (+)-(2S,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N₄-acetylcystosine
• CAS No.: 136794-49-5
• Molecular Formula: C₂₆H₃₁N₃O₄SSi
• Molecular Weight: 509.701

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

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

Chemical Property:

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

There total 10 articles about (+)-(2S,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N₄-acetylcystosine 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: 43.0%

<2S(2α,5α)>- and <2S(2α,5β)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-ol acetate (202532-88-5) + N4-acetyl-O-trimethylsilylcytosine (54230-57-8) → (-)-(2S,5S)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N4-acetylcystosine (136846-19-0) + (+)-(2S,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N4-acetylcystosine (136794-49-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; Ambient temperature;

DOI:10.1021/jm00070a006

Reference yield:

(-)-<2S(2α,5α)>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane-5-carboxylic acid (140630-83-7) → (+)-(2S,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N4-acetylcystosine (136794-49-5)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 43 percent / trimethylsilyl triflate / 1,2-dichloro-ethane / Ambient temperature

With pyridine; trimethylsilyl trifluoromethanesulfonate; In ethyl acetate; 1,2-dichloro-ethane;

DOI:10.1021/jm00070a006

Reference yield:

(2S,5S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]oxathiolane-5-carbaldehyde (148774-90-7) → (+)-(2S,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N4-acetylcystosine (136794-49-5)

Guidance literature:

Multi-step reaction with 6 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

6: 43 percent / trimethylsilyl triflate / 1,2-dichloro-ethane / Ambient temperature

With pyridine; lithium hydroxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; trimethylsilyl trifluoromethanesulfonate; dichloroborane-dimethyl sulfide; potassium carbonate; In tetrahydrofuran; water; ethyl acetate; 1,2-dichloro-ethane; acetone; acetonitrile;

DOI:10.1021/jm00070a006

upstream raw materials:

4-N-Acetylcytosine

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

N⁴-acetyl-O-trimethylsilylcytosine

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

Downstream raw materials:

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

lamivudine

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