(RS)-[(2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxypyrrolidin-2-yl]-(1-methyl-2-phenylthioimidazol-5-yl)methanol

Base Information

Chemical Name:(RS)-[(2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxypyrrolidin-2-yl]-(1-methyl-2-phenylthioimidazol-5-yl)methanol
CAS No.:351529-72-1
Molecular Formula:C₂₈H₃₉N₃O₂SSi
Molecular Weight:509.788
Hs Code.:

Synonyms:(RS)-[(2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxypyrrolidin-2-yl]-(1-methyl-2-phenylthioimidazol-5-yl)methanol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (RS)-[(2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxypyrrolidin-2-yl]-(1-methyl-2-phenylthioimidazol-5-yl)methanol

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Technology Process of (RS)-[(2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxypyrrolidin-2-yl]-(1-methyl-2-phenylthioimidazol-5-yl)methanol

There total 1 articles about (RS)-[(2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxypyrrolidin-2-yl]-(1-methyl-2-phenylthioimidazol-5-yl)methanol 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: 56.0%

: 79487-95-9
1-methyl-2-phenylsulfanyl-1H-imidazole

: 156440-98-1
(2S,4R)-N-benzyl-4-(tert-butyldimethylsilyloxy)pyrrolidine-2-carbaldehyde

: 351529-72-1
(RS)-[(2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxypyrrolidin-2-yl]-(1-methyl-2-phenylthioimidazol-5-yl)methanol

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; at -68 - -5 ℃; for 2.5h;
DOI:10.1016/S0968-0896(00)00314-X

Reference yield: 76.4%

: 351529-72-1
(RS)-[(2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxypyrrolidin-2-yl]-(1-methyl-2-phenylthioimidazol-5-yl)methanol

: 191734-26-6
(RS)-[(2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxypyrrolidin-2-yl]-(1-methylimidazol-5-yl)methanol

Guidance literature:: With nickel; In ethanol; at 20 ℃; for 2.5h;
DOI:10.1016/S0968-0896(00)00314-X

Reference yield:

: 351529-72-1
(RS)-[(2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxypyrrolidin-2-yl]-(1-methyl-2-phenylthioimidazol-5-yl)methanol

: 156442-06-7
(2R,4S)-1-Allyloxycarbonyl-4-benzoylthio-2-(1-methyl-imidazol-5-ylmethyl)-pyrrolidine

Guidance literature:: Multi-step reaction with 8 steps

1: 76.4 percent / Raney-Ni / ethanol / 2.5 h / 20 °C

2: SOCl₂ / 1 h / -20 °C

3: 211.7 g / Et₃N / CH₂Cl₂ / 1 h / -15 - -5 °C

4: 130.7 g / AIBN; n-Bu₃SnH / toluene / 1.75 h / Heating

5: HCO₂NH₄ / Pd/C / methanol / 0.67 h / Heating

6: 66.2 g / aq. NaOH / tetrahydrofuran / 0.17 h / 0 - 5 °C / pH 8.5 - 10

7: aq. HCl / methanol / 1.75 h / 0 - 20 °C

8: 98 percent / PPh₃; DEAD / tetrahydrofuran / 2 h / 20 °C

With hydrogenchloride; sodium hydroxide; thionyl chloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; ammonium formate; nickel; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene; 8: Mitsunobu reaction;
DOI:10.1016/S0968-0896(00)00314-X