(1S/R,2S,4R)-1-O-aceyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranoside

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Chemical Name:(1S/R,2S,4R)-1-O-aceyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranoside
CAS No.:398133-34-1
Molecular Formula:C₂₉H₃₃FO₃SSeSi
Molecular Weight:587.689
Hs Code.:
Mol file:398133-34-1.mol

Synonyms:(1S/R,2S,4R)-1-O-aceyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranoside

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Chemical Property of (1S/R,2S,4R)-1-O-aceyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranoside Edit

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Technology Process of (1S/R,2S,4R)-1-O-aceyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranoside

There total 25 articles about (1S/R,2S,4R)-1-O-aceyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranoside 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:

: 108-24-7
acetic anhydride

: (3S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-fluoro-3-phenylselanyl-tetrahydro-thiophen-2-ol

: 398133-34-1
(1S/R,2S,4R)-1-O-aceyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranoside

Guidance literature:: DOI:10.1081/NCN-120021965

Reference yield:

: 212954-52-4
(R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-fluoro-5H-furan-2-one

: 398133-34-1
(1S/R,2S,4R)-1-O-aceyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: H₂ / Pd/C

2.1: NaOH

3.1: I₂; PPh₃; imidazole

4.1: dimethylformamide

5.1: DIBAL-H

5.2: acetic anhydride / dimethylsulfoxide

6.1: LiHMDS

6.2: TMSCl

7.1: DIBAL-H

With 1H-imidazole; sodium hydroxide; hydrogen; iodine; diisobutylaluminium hydride; triphenylphosphine; lithium hexamethyldisilazane; palladium on activated charcoal; In N,N-dimethyl-formamide;
DOI:10.1081/NCN-120021965

Reference yield:

: 212954-52-4
(R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-fluoro-5H-furan-2-one

: 398133-34-1
(1S/R,2S,4R)-1-O-aceyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: 100 percent / H₂ / Pd⁽⁰⁾ / ethyl acetate

2.1: NaOH / aq. ethanol

2.2: dimethylsulfoxide

2.3: 83 percent / I₂; Ph₃P; imidazole / toluene / 4 h / 60 °C

3.1: 91 percent / dimethylformamide

4.1: DIBAL-H / toluene / -78 °C

5.1: Ac₂O; DMSO

6.1: 74 percent / LiHMDS; TMSCl / tetrahydrofuran / -78 °C

7.1: DIBAL-H / toluene / -78 °C

8.1: TEA / CH₂Cl₂

With sodium hydroxide; chloro-trimethyl-silane; TEA; hydrogen; acetic anhydride; diisobutylaluminium hydride; dimethyl sulfoxide; lithium hexamethyldisilazane; palladium; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; 5.1: Moffatt oxidation;
DOI:10.1021/ol0171665