(4S)-4-[(1'S,3'Z)-5'-hydroxy-1'-phenylsulfonyloxy-3'-pentenyl]-2,2-dimethyl-1,3-dioxolane

Base Information

Chemical Name:(4S)-4-[(1'S,3'Z)-5'-hydroxy-1'-phenylsulfonyloxy-3'-pentenyl]-2,2-dimethyl-1,3-dioxolane
CAS No.:532932-78-8
Molecular Formula:C₁₆H₂₂O₆S
Molecular Weight:342.413
Hs Code.:

Synonyms:(4S)-4-[(1'S,3'Z)-5'-hydroxy-1'-phenylsulfonyloxy-3'-pentenyl]-2,2-dimethyl-1,3-dioxolane

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Chemical Property of (4S)-4-[(1'S,3'Z)-5'-hydroxy-1'-phenylsulfonyloxy-3'-pentenyl]-2,2-dimethyl-1,3-dioxolane

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Technology Process of (4S)-4-[(1'S,3'Z)-5'-hydroxy-1'-phenylsulfonyloxy-3'-pentenyl]-2,2-dimethyl-1,3-dioxolane

There total 4 articles about (4S)-4-[(1'S,3'Z)-5'-hydroxy-1'-phenylsulfonyloxy-3'-pentenyl]-2,2-dimethyl-1,3-dioxolane 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: 94.0%

: 532932-77-7
(4S)-4-[(1'S)-5'-hydroxy-1'-phenylsulfonyloxy-3'-pentynyl]-2,2-dimethyl-1,3-dioxolane

: 532932-78-8
(4S)-4-[(1'S,3'Z)-5'-hydroxy-1'-phenylsulfonyloxy-3'-pentenyl]-2,2-dimethyl-1,3-dioxolane

Guidance literature:: With quinoline; hydrogen; Lindlar's catalyst; In ethyl acetate; at 20 ℃; for 6h;
DOI:10.1016/S0957-4166(03)00038-7

Reference yield:

: 93367-10-3,212375-57-0
(2S,3S)-3,4-epoxy-1,2-di-O-isopropylidenebutane-1,2-diol

: 532932-78-8
(4S)-4-[(1'S,3'Z)-5'-hydroxy-1'-phenylsulfonyloxy-3'-pentenyl]-2,2-dimethyl-1,3-dioxolane

Guidance literature:: Multi-step reaction with 4 steps

1: 51 percent / n-BuLi; BF₃*Et₂O / tetrahydrofuran; hexane / 6 h / -78 °C

2: 80 percent / Et₃N / CH₂Cl₂ / 6 h / 20 °C

3: 71 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C

4: 94 percent / quinoline; H₂ / Lindlar's catalyst / ethyl acetate / 6 h / 20 °C

With quinoline; n-butyllithium; boron trifluoride diethyl etherate; hydrogen; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Lindlar's catalyst; In tetrahydrofuran; hexane; dichloromethane; water; ethyl acetate;
DOI:10.1016/S0957-4166(03)00038-7

Reference yield:

: 532932-75-5
(1S)-1-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-5-(4-methoxybenzyloxy)-3-pentyn-1-ol

: 532932-78-8
(4S)-4-[(1'S,3'Z)-5'-hydroxy-1'-phenylsulfonyloxy-3'-pentenyl]-2,2-dimethyl-1,3-dioxolane

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent / Et₃N / CH₂Cl₂ / 6 h / 20 °C

2: 71 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C

3: 94 percent / quinoline; H₂ / Lindlar's catalyst / ethyl acetate / 6 h / 20 °C

With quinoline; hydrogen; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Lindlar's catalyst; In dichloromethane; water; ethyl acetate;
DOI:10.1016/S0957-4166(03)00038-7