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

Base Information

Chemical Name:(8R,8aS)-7-<<(Dimethylethyl)dimethylsilyl>oxy>-8-hydroxy-8-methyl-6-<(Z)-2(R)-methyl-4-(benzyloxy)butylidene>octahydroindolizine
CAS No.:91550-15-1
Molecular Formula:C₂₇H₄₅NO₃Si
Molecular Weight:459.745
Hs Code.:

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

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Chemical Property of (8R,8aS)-7-<<(Dimethylethyl)dimethylsilyl>oxy>-8-hydroxy-8-methyl-6-<(Z)-2(R)-methyl-4-(benzyloxy)butylidene>octahydroindolizine

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Technology Process of (8R,8aS)-7-<<(Dimethylethyl)dimethylsilyl>oxy>-8-hydroxy-8-methyl-6-<(Z)-2(R)-methyl-4-(benzyloxy)butylidene>octahydroindolizine

There total 15 articles about (8R,8aS)-7-<<(Dimethylethyl)dimethylsilyl>oxy>-8-hydroxy-8-methyl-6-<(Z)-2(R)-methyl-4-(benzyloxy)butylidene>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: 49.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 138053-03-9
(8R,8aS)-8-Hydroxy-8-methyl-6-<(Z)-2(R)-methyl-4-(benzyloxy)butylidene>octahydroindolizin-7-ol

: 91550-15-1
(8R,8aS)-7-<<(Dimethylethyl)dimethylsilyl>oxy>-8-hydroxy-8-methyl-6-<(Z)-2(R)-methyl-4-(benzyloxy)butylidene>octahydroindolizine

Guidance literature:: With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; at -78 ℃;
DOI:10.1021/ja00330a059

Reference yield:

: 91550-09-3
(R)-α-Methyl-α-(1-methoxypropadienyl)-2(S)-pyrrolidinemethanol

: 91550-15-1
(8R,8aS)-7-<<(Dimethylethyl)dimethylsilyl>oxy>-8-hydroxy-8-methyl-6-<(Z)-2(R)-methyl-4-(benzyloxy)butylidene>octahydroindolizine

Guidance literature:: Multi-step reaction with 6 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

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:

: 91550-14-0
(2R)-4-(Benzyloxy)-2-methyl-1-butanal

: 91550-15-1
(8R,8aS)-7-<<(Dimethylethyl)dimethylsilyl>oxy>-8-hydroxy-8-methyl-6-<(Z)-2(R)-methyl-4-(benzyloxy)butylidene>octahydroindolizine

Guidance literature:: Multi-step reaction with 4 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

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