[1'R,2'S,3'R,5R]-5-[3'-(t-butyldimethylsilyloxy)-1',2'-isopropylidenedioxy-3'-phenylpropyl]-4-phenylsulfonylbutan-4-olide

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Chemical Name:[1'R,2'S,3'R,5R]-5-[3'-(t-butyldimethylsilyloxy)-1',2'-isopropylidenedioxy-3'-phenylpropyl]-4-phenylsulfonylbutan-4-olide
CAS No.:252273-51-1
Molecular Formula:C₂₈H₃₈O₇SSi
Molecular Weight:546.757
Hs Code.:

Synonyms:[1'R,2'S,3'R,5R]-5-[3'-(t-butyldimethylsilyloxy)-1',2'-isopropylidenedioxy-3'-phenylpropyl]-4-phenylsulfonylbutan-4-olide

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Chemical Property of [1'R,2'S,3'R,5R]-5-[3'-(t-butyldimethylsilyloxy)-1',2'-isopropylidenedioxy-3'-phenylpropyl]-4-phenylsulfonylbutan-4-olide

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Technology Process of [1'R,2'S,3'R,5R]-5-[3'-(t-butyldimethylsilyloxy)-1',2'-isopropylidenedioxy-3'-phenylpropyl]-4-phenylsulfonylbutan-4-olide

There total 6 articles about [1'R,2'S,3'R,5R]-5-[3'-(t-butyldimethylsilyloxy)-1',2'-isopropylidenedioxy-3'-phenylpropyl]-4-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: 94.0%

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

: 252273-51-1
[1'R,2'S,3'R,5R]-5-[3'-(t-butyldimethylsilyloxy)-1',2'-isopropylidenedioxy-3'-phenylpropyl]-4-phenylsulfonylbutan-4-olide

Guidance literature:: With (1S)-10-camphorsulfonic acid; In toluene; for 1.5h; Heating;
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

: 252273-51-1
[1'R,2'S,3'R,5R]-5-[3'-(t-butyldimethylsilyloxy)-1',2'-isopropylidenedioxy-3'-phenylpropyl]-4-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: 94 percent / camphorsulfonic acid / toluene / 1 h / Heating

With lithium aluminium tetrahydride; n-butyllithium; camphor-10-sulfonic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; 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

: 252273-51-1
[1'R,2'S,3'R,5R]-5-[3'-(t-butyldimethylsilyloxy)-1',2'-isopropylidenedioxy-3'-phenylpropyl]-4-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: 94 percent / camphorsulfonic acid / toluene / 1 h / Heating

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