[1'R,2'R,3'R,4S]-4-(3-phenyl-1',2',3'-trihydroxypropyl)-3-phenylsulfonylbutan-4-olide

Base Information

Chemical Name:[1'R,2'R,3'R,4S]-4-(3-phenyl-1',2',3'-trihydroxypropyl)-3-phenylsulfonylbutan-4-olide
CAS No.:252273-49-7
Molecular Formula:C₁₉H₂₀O₇S
Molecular Weight:392.43
Hs Code.:

Synonyms:[1'R,2'R,3'R,4S]-4-(3-phenyl-1',2',3'-trihydroxypropyl)-3-phenylsulfonylbutan-4-olide

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Chemical Property of [1'R,2'R,3'R,4S]-4-(3-phenyl-1',2',3'-trihydroxypropyl)-3-phenylsulfonylbutan-4-olide

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Technology Process of [1'R,2'R,3'R,4S]-4-(3-phenyl-1',2',3'-trihydroxypropyl)-3-phenylsulfonylbutan-4-olide

There total 7 articles about [1'R,2'R,3'R,4S]-4-(3-phenyl-1',2',3'-trihydroxypropyl)-3-phenylsulfonylbutan-4-olide 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: 85.0%

: 252273-48-6
trimethyl (4R,5R,6S,7R)-7-(t-butyldimethylsilyloxy)-5,6-isopropylidenedioxy-3-phenylsulfonyl-7-phenylorthoheptanoate

: 252273-49-7
[1'R,2'R,3'R,4S]-4-(3-phenyl-1',2',3'-trihydroxypropyl)-3-phenylsulfonylbutan-4-olide

Guidance literature:: With hydrogenchloride; acetic acid; In tetrahydrofuran; at 65 ℃; for 3h;
DOI:10.1016/0040-4039(96)00820-9

Reference yield:

: 179618-34-9
ethyl (2S,3S,4R)-4-{[(tert-butyl)(dimethyl)silyl]oxy}-2,3-dihydroxy-4-phenylbutanoate

: 252273-49-7
[1'R,2'R,3'R,4S]-4-(3-phenyl-1',2',3'-trihydroxypropyl)-3-phenylsulfonylbutan-4-olide

Guidance literature:: Multi-step reaction with 4 steps

1: 99 percent / camphorsulfonic acid / CH₂Cl₂ / 0.25 h / 20 °C

2: 93 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -78 - 20 °C

3: 96 percent / LiAlH₄ / diethyl ether / 1 h / -78 °C

4: HCl / acetic acid; tetrahydrofuran; H₂O / 2.5 h / Heating

With hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; camphor-10-sulfonic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetic acid; 1: Cyclization / 2: Julia coupling / 3: Reduction / 4: Cyclization;
DOI:10.1016/S0040-4020(99)00794-2

Reference yield:

: 179618-33-8
ethyl (2E,4S)-4-{[(tert-butyl)(dimethyl)silyl]oxy}-4-phenylbut-2-enoate

: 252273-49-7
[1'R,2'R,3'R,4S]-4-(3-phenyl-1',2',3'-trihydroxypropyl)-3-phenylsulfonylbutan-4-olide

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / AD-mix-β; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 14 h / 20 °C

2: 99 percent / camphorsulfonic acid / CH₂Cl₂ / 0.25 h / 20 °C

3: 93 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -78 - 20 °C

4: 96 percent / LiAlH₄ / diethyl ether / 1 h / -78 °C

5: HCl / acetic acid; tetrahydrofuran; H₂O / 2.5 h / Heating

With hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; methanesulfonamide; AD-mix-β; camphor-10-sulfonic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetic acid; tert-butyl alcohol; 1: hydroxylation / 2: Cyclization / 3: Julia coupling / 4: Reduction / 5: Cyclization;
DOI:10.1016/S0040-4020(99)00794-2