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

Base Information

• Chemical Name: trimethyl (5S,6S,7R)-7-(t-butyldimethylsilyloxy)-5,6-isopropylidenedioxy-4-oxo-3-phenylsulfonyl-7-phenylorthoheptanoate
• CAS No.: 252273-46-4
• Molecular Formula: C₃₁H₄₆O₉SSi
• Molecular Weight: 622.852
• Mol file: 252273-46-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about trimethyl (5S,6S,7R)-7-(t-butyldimethylsilyloxy)-5,6-isopropylidenedioxy-4-oxo-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: 93.0%

trimethyl 3-(phenylsulfonyl)orthopropionate (38435-08-4) + ethyl (4S,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate (187931-99-3) → trimethyl (5S,6S,7R)-7-(t-butyldimethylsilyloxy)-5,6-isopropylidenedioxy-4-oxo-3-phenylsulfonyl-7-phenylorthoheptanoate (252273-46-4)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 3h;

DOI:10.1016/S0040-4020(99)00794-2

Reference yield:

ethyl (2S,3S,4R)-4-{[(tert-butyl)(dimethyl)silyl]oxy}-2,3-dihydroxy-4-phenylbutanoate (179618-34-9) → trimethyl (5S,6S,7R)-7-(t-butyldimethylsilyloxy)-5,6-isopropylidenedioxy-4-oxo-3-phenylsulfonyl-7-phenylorthoheptanoate (252273-46-4)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With n-butyllithium; camphor-10-sulfonic acid; In tetrahydrofuran; hexane; dichloromethane; 1: Cyclization / 2: Julia coupling;

DOI:10.1016/S0040-4020(99)00794-2

Reference yield:

ethyl (2E,4S)-4-{[(tert-butyl)(dimethyl)silyl]oxy}-4-phenylbut-2-enoate (179618-33-8) → trimethyl (5S,6S,7R)-7-(t-butyldimethylsilyloxy)-5,6-isopropylidenedioxy-4-oxo-3-phenylsulfonyl-7-phenylorthoheptanoate (252273-46-4)

Guidance literature:

Multi-step reaction with 3 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

With n-butyllithium; methanesulfonamide; AD-mix-β; camphor-10-sulfonic acid; In tetrahydrofuran; hexane; dichloromethane; water; tert-butyl alcohol; 1: hydroxylation / 2: Cyclization / 3: Julia coupling;

DOI:10.1016/S0040-4020(99)00794-2

upstream raw materials:

trimethyl 3-(phenylsulfonyl)orthopropionate

ethyl (4S,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate

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

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

Downstream raw materials:

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

(+)-goniofufurone

(5S,6R)-6-[(1S,2R)-1-(benzyloxy)-1,2-dihydroxy-2-phenylethyl]-5-hydroxy-5,6-dihydro-2H-pyran-2-one

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