((1S,2S)-1-Benzyl-2-hydroxy-4-phenylsulfanyl-hex-5-enyl)-carbamic acid benzyl ester

Base Information

Chemical Name:((1S,2S)-1-Benzyl-2-hydroxy-4-phenylsulfanyl-hex-5-enyl)-carbamic acid benzyl ester
CAS No.:199392-52-4
Molecular Formula:C₂₇H₂₉NO₃S
Molecular Weight:447.598
Hs Code.:

Synonyms:((1S,2S)-1-Benzyl-2-hydroxy-4-phenylsulfanyl-hex-5-enyl)-carbamic acid benzyl ester

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Chemical Property of ((1S,2S)-1-Benzyl-2-hydroxy-4-phenylsulfanyl-hex-5-enyl)-carbamic acid benzyl ester

Chemical Property:

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Technology Process of ((1S,2S)-1-Benzyl-2-hydroxy-4-phenylsulfanyl-hex-5-enyl)-carbamic acid benzyl ester

There total 1 articles about ((1S,2S)-1-Benzyl-2-hydroxy-4-phenylsulfanyl-hex-5-enyl)-carbamic acid benzyl ester 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:

: 5296-64-0
allyl phenyl thioether

: 198020-19-8
(2R,2S)-(3S)-1,2-epoxy-3-phenylmethoxycarbonylamino-4-phenylbutane

: 199392-52-4
((1S,2S)-1-Benzyl-2-hydroxy-4-phenylsulfanyl-hex-5-enyl)-carbamic acid benzyl ester

Guidance literature:: With n-butyllithium; Yield given. Multistep reaction; 1.) THF, -78 deg C, 4 h, 2.) THF, -78 deg C, 3 h;
DOI:10.1055/s-1997-1347

Reference yield: 97.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 199392-52-4
((1S,2S)-1-Benzyl-2-hydroxy-4-phenylsulfanyl-hex-5-enyl)-carbamic acid benzyl ester

: 199392-53-5
[(1S,2S)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-phenylsulfanyl-hex-5-enyl]-carbamic acid benzyl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; Ambient temperature;
DOI:10.1055/s-1997-1347

Reference yield:

: 199392-52-4
((1S,2S)-1-Benzyl-2-hydroxy-4-phenylsulfanyl-hex-5-enyl)-carbamic acid benzyl ester

: 125356-66-3,119463-16-0
(+)-preussin

Guidance literature:: Multi-step reaction with 9 steps

1: 97 percent / imidazole / dimethylformamide / Ambient temperature

2: NaIO₄ / methanol; H₂O / 36 h

3: 88 percent / P(OMe)3 / methanol / 48 h

4: 45 percent / Ti(Oi-Pr)4, t-BuOOH, D-(-)-DET / CH₂Cl₂; toluene / 36 h / -23 °C

5: 83 percent / NaIO₄ / CH₂Cl₂; H₂O / 8 h / 32 °C

6: 1.) KHMDS / 1.) THF, DMSO, 0 deg C, 1 h, 2.) THF, DMSO, a) -78 deg C, 30 min, b) 40 deg C, 8 h

7: 99 percent / TBAF*3H₂O / tetrahydrofuran / Ambient temperature

8: 91 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

9: 98 percent / H₂ / 10percent Pd/C / ethanol / 760 Torr

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; lithium aluminium tetrahydride; diethyl (2S,3S)-tartrate; tetrabutyl ammonium fluoride; hydrogen; potassium hexamethylsilazane; phosphorous acid trimethyl ester; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1055/s-1997-1347