1β-hydroxy-2,4Hβ-13-phenylsulfonyl-11,12-dihydro-3α,10α-oxido-2α,20α-oxido-12-nortaxane-12-one

Base Information

• Chemical Name: 1β-hydroxy-2,4Hβ-13-phenylsulfonyl-11,12-dihydro-3α,10α-oxido-2α,20α-oxido-12-nortaxane-12-one
• CAS No.: 185013-21-2
• Molecular Formula: C₂₅H₃₂O₆S
• Molecular Weight: 460.591
• Mol file: 185013-21-2.mol

Synonyms:1β-hydroxy-2,4Hβ-13-phenylsulfonyl-11,12-dihydro-3α,10α-oxido-2α,20α-oxido-12-nortaxane-12-one

Chemical Property of 1β-hydroxy-2,4Hβ-13-phenylsulfonyl-11,12-dihydro-3α,10α-oxido-2α,20α-oxido-12-nortaxane-12-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1β-hydroxy-2,4Hβ-13-phenylsulfonyl-11,12-dihydro-3α,10α-oxido-2α,20α-oxido-12-nortaxane-12-one

There total 8 articles about 1β-hydroxy-2,4Hβ-13-phenylsulfonyl-11,12-dihydro-3α,10α-oxido-2α,20α-oxido-12-nortaxane-12-one 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: 100.0%

methyl 1β-hydroxy-1α-(2'-phenylsulfonylethyl)-3α,10α-oxido-2α,13α-oxido-8β,12,12-trimethylbicyclo<6.4.03,8>dodec-11α-oate (166534-11-8) → 1β-hydroxy-2,4Hβ-13-phenylsulfonyl-11,12-dihydro-3α,10α-oxido-2α,20α-oxido-12-nortaxane-12-one (185013-21-2)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at 67 ℃;

DOI:10.1016/0040-4020(96)00866-6

Reference yield:

C26H36O7S → 1β-hydroxy-2,4Hβ-13-phenylsulfonyl-11,12-dihydro-3α,10α-oxido-2α,20α-oxido-12-nortaxane-12-one (185013-21-2)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at 65 ℃; Yield given;

DOI:10.1016/00404-0399(50)1084U-

Reference yield:

11α-cyano-1β-hydroxy-1α-(2'-phenylsulfonylethyl)-3α,10α-oxido-2α,13α-oxido-8β,12,12-trimethylbicyclo<6.4.03,8>dodecane (166534-10-7) → 1β-hydroxy-2,4Hβ-13-phenylsulfonyl-11,12-dihydro-3α,10α-oxido-2α,20α-oxido-12-nortaxane-12-one (185013-21-2)

Guidance literature:

Multi-step reaction with 5 steps

1: DIBAL-H / CH₂Cl₂; toluene / 5 h / -78 °C

2: aq. HCl, aq. Rochelles salt / CH₂Cl₂; toluene / -78 °C

3: aq. NaClO₂, 2-methyl-2-butene, aq. NaH₂PO₄ / 2-methyl-propan-2-ol / 3 h / 60 °C

4: K₂CO₃ / acetone / 2 h / 22 °C

5: 100 percent / LiN(TMS)2 / tetrahydrofuran / 67 °C

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; diisobutylaluminium hydride; potassium carbonate; rochelle salt; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; acetone; toluene; tert-butyl alcohol;

DOI:10.1016/0040-4020(96)00866-6

upstream raw materials:

methyl 1β-hydroxy-1α-(2'-phenylsulfonylethyl)-3α,10α-oxido-2α,13α-oxido-8β,12,12-trimethylbicyclo<6.4.0^3,8>dodec-11α-oate

11α-cyano-1β-hydroxy-1α-(2'-phenylsulfonylethyl)-3α,10α-oxido-2α,13α-oxido-8β,12,12-trimethylbicyclo<6.4.0^3,8>dodecane

(1S,2R,6S,8R,9R,11S)-11-(2-Benzenesulfonyl-ethyl)-11-hydroxy-6,10,10-trimethyl-12-oxo-2-triisopropylsilanyloxymethyl-13-oxa-tricyclo[6.4.1.0^1,6]tridecane-9-carbonitrile