(8S,8aS)-8-hydroxy-8-methyl-6(Z)-<6-oxo-2(R),5-dimethyl-7(R)-(tert-butyldiphenylsiloxy)-4(E)-octenylidene>octahydroindolizidine

Base Information

• Chemical Name: (8S,8aS)-8-hydroxy-8-methyl-6(Z)-<6-oxo-2(R),5-dimethyl-7(R)-(tert-butyldiphenylsiloxy)-4(E)-octenylidene>octahydroindolizidine
• CAS No.: 90246-49-4
• Molecular Formula: C₃₅H₄₉NO₃Si
• Molecular Weight: 559.864
• Mol file: 90246-49-4.mol

Synonyms:(8S,8aS)-8-hydroxy-8-methyl-6(Z)-<6-oxo-2(R),5-dimethyl-7(R)-(tert-butyldiphenylsiloxy)-4(E)-octenylidene>octahydroindolizidine

Chemical Property of (8S,8aS)-8-hydroxy-8-methyl-6(Z)-<6-oxo-2(R),5-dimethyl-7(R)-(tert-butyldiphenylsiloxy)-4(E)-octenylidene>octahydroindolizidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (8S,8aS)-8-hydroxy-8-methyl-6(Z)-<6-oxo-2(R),5-dimethyl-7(R)-(tert-butyldiphenylsiloxy)-4(E)-octenylidene>octahydroindolizidine

There total 24 articles about (8S,8aS)-8-hydroxy-8-methyl-6(Z)-<6-oxo-2(R),5-dimethyl-7(R)-(tert-butyldiphenylsiloxy)-4(E)-octenylidene>octahydroindolizidine 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: 71.0%

(R)-2-((tert-butyldiphenylsilyl)oxy)-4-(triphenylphosphoranylidene)-3-pentanone (90246-35-8) + (8S,8aS)-8-hydroxy-8-methyl-6(Z)-<4-oxo-2(R)-methylbutylidene>octahydroindolizidine (90246-48-3) → (8S,8aS)-8-hydroxy-8-methyl-6(Z)-<6-oxo-2(R),5-dimethyl-7(R)-(tert-butyldiphenylsiloxy)-4(E)-octenylidene>octahydroindolizidine (90246-49-4) + Triphenylphosphine oxide (791-28-6)

Guidance literature:

In dichloromethane; for 120h; Yields of byproduct given; Heating;

DOI:10.1021/ja00327a022

Reference yield:

chloroformate ester of 5-(benzyloxy)-1-pentyn-3-ol → (8S,8aS)-8-hydroxy-8-methyl-6(Z)-<6-oxo-2(R),5-dimethyl-7(R)-(tert-butyldiphenylsiloxy)-4(E)-octenylidene>octahydroindolizidine (90246-49-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 37 percent

2: 67 percent / Cl₃SiH

3: 65 percent / diethyl ether / 0.5 h / Heating

4: 85 percent / 4-(dimethylamino)pyridine, pyridine

5: 1) CuI / 1) ether, 2) THF, 23 deg C, 10 min

6: 1) i-Bu₂AlH, MeLi / 1) hexane, THF, 23 deg C, 0.5+0.5 h, 2) THF, 60 deg C, 25 h

7: KOH / ethanol / 12 h / 90 °C

8: 496 mg / H₂O; methanol / 4 h / 23 °C

9: 52 percent / paraformaldehyde, camphorsulfonic acid / acetonitrile / 13 h / 80 °C

10: 61 percent / Li, NH₃ / tetrahydrofuran / 3 h

11: 88 percent / oxalyl chloride / dimethylsulfoxide

12: 71 percent / CH₂Cl₂ / 120 h / Heating

With pyridine; dmap; potassium hydroxide; copper(l) iodide; formaldehyd; oxalyl dichloride; camphor-10-sulfonic acid; trichlorosilane; ammonia; methyllithium; lithium; diisobutylaluminium hydride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile;

DOI:10.1021/ja00327a022

Reference yield:

(2S)-N-Benzyloxycarbony-2-(1'-hydroxy-1'-methylethyl)pyrrolidine (51207-68-2) → (8S,8aS)-8-hydroxy-8-methyl-6(Z)-<6-oxo-2(R),5-dimethyl-7(R)-(tert-butyldiphenylsiloxy)-4(E)-octenylidene>octahydroindolizidine (90246-49-4)

Guidance literature:

Multi-step reaction with 9 steps

1: SOCl₂, Et₃N / tetrahydrofuran / 0.5 h / -50 - -45 °C

2: 37 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 3 h / 25 °C

3: 1) i-Bu₂AlH, MeLi / 1) hexane, THF, 23 deg C, 0.5+0.5 h, 2) THF, 60 deg C, 25 h

4: KOH / ethanol / 12 h / 90 °C

5: 496 mg / H₂O; methanol / 4 h / 23 °C

6: 52 percent / paraformaldehyde, camphorsulfonic acid / acetonitrile / 13 h / 80 °C

7: 61 percent / Li, NH₃ / tetrahydrofuran / 3 h

8: 88 percent / oxalyl chloride / dimethylsulfoxide

9: 71 percent / CH₂Cl₂ / 120 h / Heating

With potassium hydroxide; formaldehyd; thionyl chloride; oxalyl dichloride; camphor-10-sulfonic acid; ammonia; methyllithium; lithium; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile;

DOI:10.1021/ja00327a022

upstream raw materials:

(R)-2-((tert-butyldiphenylsilyl)oxy)-4-(triphenylphosphoranylidene)-3-pentanone

(8S,8aS)-8-hydroxy-8-methyl-6(Z)-<4-oxo-2(R)-methylbutylidene>octahydroindolizidine

(2S)-N-Benzyloxycarbony-2-(1'-hydroxy-1'-methylethyl)pyrrolidine

(2S)-N-Benzyloxycarbony-2-(1'-methylethenyl)pyrrolidine

Downstream raw materials:

Pumiliotoxin B