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

Base Information

Chemical Name:trimethyl (4R,5R,6S,7R)-7-(t-butyldimethylsilyloxy)-5,6-isopropylidenedioxy-3-phenylsulfonyl-7-phenylorthoheptanoate
CAS No.:252273-48-6
Molecular Formula:C₃₁H₄₈O₉SSi
Molecular Weight:624.868
Hs Code.:

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

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Chemical Property of trimethyl (4R,5R,6S,7R)-7-(t-butyldimethylsilyloxy)-5,6-isopropylidenedioxy-3-phenylsulfonyl-7-phenylorthoheptanoate

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Technology Process of trimethyl (4R,5R,6S,7R)-7-(t-butyldimethylsilyloxy)-5,6-isopropylidenedioxy-3-phenylsulfonyl-7-phenylorthoheptanoate

There total 5 articles about trimethyl (4R,5R,6S,7R)-7-(t-butyldimethylsilyloxy)-5,6-isopropylidenedioxy-3-phenylsulfonyl-7-phenylorthoheptanoate 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: 96.0%

: 252273-46-4
trimethyl (5S,6S,7R)-7-(t-butyldimethylsilyloxy)-5,6-isopropylidenedioxy-4-oxo-3-phenylsulfonyl-7-phenylorthoheptanoate

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

Guidance literature:: With lithium aluminium tetrahydride; In diethyl ether; at -78 ℃; for 2h;
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

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

Guidance literature:: Multi-step reaction with 3 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

With lithium aluminium tetrahydride; n-butyllithium; camphor-10-sulfonic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1: Cyclization / 2: Julia coupling / 3: Reduction;
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

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

Guidance literature:: Multi-step reaction with 4 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

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