(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

Base Information

• Chemical Name: (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
• CAS No.: 185013-20-1
• Molecular Formula: C₃₄H₅₃NO₆SSi
• Molecular Weight: 631.949
• Mol file: 185013-20-1.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 1 articles about (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 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:

(1S,2R,6S,8R,9R,11R)-11-(2-Benzenesulfonyl-ethyl)-6,10,10-trimethyl-12-oxo-2-triisopropylsilanyloxymethyl-13-oxa-tricyclo[6.4.1.01,6]tridecane-9-carbonitrile → (1S,2R,6S,8R,9R,11S)-11-(2-Benzenesulfonyl-ethyl)-11-hydroxy-6,10,10-trimethyl-12-oxo-2-triisopropylsilanyloxymethyl-13-oxa-tricyclo[6.4.1.01,6]tridecane-9-carbonitrile (185013-20-1)

Guidance literature:

With potassium tert-butylate; oxygen; triethyl phosphite; Yield given. Multistep reaction; 1.) THF, 24 deg C, 0.1 h, 2.) THF, -78 deg C, 0.75 h;

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

Reference yield: 100.0%

(1S,2R,6S,8R,9R,11S)-11-(2-Benzenesulfonyl-ethyl)-11-hydroxy-6,10,10-trimethyl-12-oxo-2-triisopropylsilanyloxymethyl-13-oxa-tricyclo[6.4.1.01,6]tridecane-9-carbonitrile (185013-20-1) → 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)

Guidance literature:

With sodium cyanoborohydride; trifluoroacetic acid; at 0 ℃; for 0.25h;

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

Reference yield:

(1S,2R,6S,8R,9R,11S)-11-(2-Benzenesulfonyl-ethyl)-11-hydroxy-6,10,10-trimethyl-12-oxo-2-triisopropylsilanyloxymethyl-13-oxa-tricyclo[6.4.1.01,6]tridecane-9-carbonitrile (185013-20-1) → 4Hβ-11,12-dihydro-1β-hydroxy-18α-(phenylthio)-3α,10α-oxido-2α,20α-oxido-taxane-13-one

Guidance literature:

Multi-step reaction with 12 steps

1: 100 percent / NaCNBH₃, TFA / 0.25 h / 0 °C

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

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

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

5: K₂CO₃ / acetone / 2 h / 22 °C

6: 100 percent / LiN(TMS)2 / tetrahydrofuran / 67 °C

7: 100 percent / Na, liq. NH₃ / tetrahydrofuran / -78 °C

8: 1.) t-BuOK, 2.) O₂ / 1.) THF, 0 deg C, 0.25 h, 2.) THF, 23 deg C, 0.25 h

9: 100 percent / K₂CO₃ / acetone / 18 h / 23 °C

10: 74 percent / tetrahydrofuran; diethyl ether / 0.25 h / 0 °C

11: 100 percent / aq. HCl / dioxane / 23 °C

12: 1,1,3,3-tetramethylguanidine / CH₂Cl₂ / 3 h / 23 °C

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; potassium tert-butylate; ammonia; oxygen; sodium; diisobutylaluminium hydride; sodium cyanoborohydride; potassium carbonate; rochelle salt; trifluoroacetic acid; lithium hexamethyldisilazane; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; acetone; toluene; tert-butyl alcohol;

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

Downstream raw materials:

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

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

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