(8R,8aS)-7-<<(Dimethylethyl)dimethylsilyl>oxy>-8-hydroxy-8-methyl-6-<(Z)-2(R),5-dimethyl-7-<<(dimethylethyl)diphenylsilyl>oxy>-6-oxo-4-octen-1-ylidene>octahydroindolizine

Base Information

• Chemical Name: (8R,8aS)-7-<<(Dimethylethyl)dimethylsilyl>oxy>-8-hydroxy-8-methyl-6-<(Z)-2(R),5-dimethyl-7-<<(dimethylethyl)diphenylsilyl>oxy>-6-oxo-4-octen-1-ylidene>octahydroindolizine
• CAS No.: 91550-17-3
• Molecular Formula: C₄₁H₆₃NO₄Si₂
• Molecular Weight: 690.127
• Mol file: 91550-17-3.mol

Synonyms:(8R,8aS)-7-<<(Dimethylethyl)dimethylsilyl>oxy>-8-hydroxy-8-methyl-6-<(Z)-2(R),5-dimethyl-7-<<(dimethylethyl)diphenylsilyl>oxy>-6-oxo-4-octen-1-ylidene>octahydroindolizine

Chemical Property of (8R,8aS)-7-<<(Dimethylethyl)dimethylsilyl>oxy>-8-hydroxy-8-methyl-6-<(Z)-2(R),5-dimethyl-7-<<(dimethylethyl)diphenylsilyl>oxy>-6-oxo-4-octen-1-ylidene>octahydroindolizine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (8R,8aS)-7-<<(Dimethylethyl)dimethylsilyl>oxy>-8-hydroxy-8-methyl-6-<(Z)-2(R),5-dimethyl-7-<<(dimethylethyl)diphenylsilyl>oxy>-6-oxo-4-octen-1-ylidene>octahydroindolizine

There total 17 articles about (8R,8aS)-7-<<(Dimethylethyl)dimethylsilyl>oxy>-8-hydroxy-8-methyl-6-<(Z)-2(R),5-dimethyl-7-<<(dimethylethyl)diphenylsilyl>oxy>-6-oxo-4-octen-1-ylidene>octahydroindolizine 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: 55.0%

(R)-2-((tert-butyldiphenylsilyl)oxy)-4-(triphenylphosphoranylidene)-3-pentanone (90246-35-8) + (8R,8aS)-7-<<(Dimethylethyl)dimethylsilyl>oxy>-8-hydroxy-8-methyl-6-<(Z)-2(R)-methyl-4-oxobutylidene>octahydroindolizine (91550-16-2) → (8R,8aS)-7-<<(Dimethylethyl)dimethylsilyl>oxy>-8-hydroxy-8-methyl-6-<(Z)-2(R),5-dimethyl-7-<<(dimethylethyl)diphenylsilyl>oxy>-6-oxo-4-octen-1-ylidene>octahydroindolizine (91550-17-3)

Guidance literature:

DOI:10.1021/ja00330a059

Reference yield:

(R)-α-Methyl-α-(1-methoxypropadienyl)-2(S)-pyrrolidinemethanol (91550-09-3) → (8R,8aS)-7-<<(Dimethylethyl)dimethylsilyl>oxy>-8-hydroxy-8-methyl-6-<(Z)-2(R),5-dimethyl-7-<<(dimethylethyl)diphenylsilyl>oxy>-6-oxo-4-octen-1-ylidene>octahydroindolizine (91550-17-3)

Guidance literature:

Multi-step reaction with 8 steps

1: p-toluenesulfonic acid / acetonitrile / 23 °C

2: 76 percent / HCl 5percent / 23 °C

3: 1.) (Ph)3Li / 1.) Et₂O, 0 deg C; 2.) Et₂O, 0 deg C

4: (CF₃COO)2O, DBU, DMAP / 0 °C

5: 58 percent / NaBH₄-CeCl₃

6: 49 percent / BuLi, HMPA / -78 °C

7: 83 percent

8: 55 percent

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; (CF₃COO)2O; (Ph)3Li; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile;

DOI:10.1021/ja00330a059

Reference yield:

(2R)-4-(Benzyloxy)-2-methyl-1-butanal (91550-14-0) → (8R,8aS)-7-<<(Dimethylethyl)dimethylsilyl>oxy>-8-hydroxy-8-methyl-6-<(Z)-2(R),5-dimethyl-7-<<(dimethylethyl)diphenylsilyl>oxy>-6-oxo-4-octen-1-ylidene>octahydroindolizine (91550-17-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) (Ph)3Li / 1.) Et₂O, 0 deg C; 2.) Et₂O, 0 deg C

2: (CF₃COO)2O, DBU, DMAP / 0 °C

3: 58 percent / NaBH₄-CeCl₃

4: 49 percent / BuLi, HMPA / -78 °C

5: 83 percent

6: 55 percent

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; (CF₃COO)2O; (Ph)3Li; 1,8-diazabicyclo[5.4.0]undec-7-ene;

DOI:10.1021/ja00330a059

upstream raw materials:

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

(8R,8aS)-7-<<(Dimethylethyl)dimethylsilyl>oxy>-8-hydroxy-8-methyl-6-<(Z)-2(R)-methyl-4-oxobutylidene>octahydroindolizine

(2R)-4-(Benzyloxy)-2-methyl-1-butanal

(R)-α-Methyl-α-(1-methoxypropadienyl)-2(S)-pyrrolidinemethanol

Downstream raw materials:

(+)-Allopumiliotoxin 339B