(R)-2-{(E)-(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-[(1R,3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexyl]-1,3-dimethyl-but-3-enyl}-oxirane

Base Information

Chemical Name:(R)-2-{(E)-(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-[(1R,3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexyl]-1,3-dimethyl-but-3-enyl}-oxirane
CAS No.:176656-10-3
Molecular Formula:C₃₇H₅₈O₄Si₂
Molecular Weight:623.036
Hs Code.:

(R)-2-{(E)-(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-[(1R,3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexyl]-1,3-dimethyl-but-3-enyl}-oxirane

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Chemical Property of (R)-2-{(E)-(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-[(1R,3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexyl]-1,3-dimethyl-but-3-enyl}-oxirane

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Technology Process of (R)-2-{(E)-(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-[(1R,3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexyl]-1,3-dimethyl-but-3-enyl}-oxirane

There total 11 articles about (R)-2-{(E)-(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-[(1R,3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexyl]-1,3-dimethyl-but-3-enyl}-oxirane 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:

: 69739-34-0
t-butyldimethylsiyl triflate

: 176656-10-3
(R)-2-{(E)-(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-[(1R,3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexyl]-1,3-dimethyl-but-3-enyl}-oxirane

Guidance literature:: Multi-step reaction with 4 steps

1: 2,6-lutidine / CH₂Cl₂ / 12 h / 0 °C

2: NMO, OsO₄ / tetrahydrofuran / 1) 0 deg C -> 15 deg C, 10 h, 2) 25 deg C, 17 h

3: 93 percent / pyridine, DMAP / 0.5 h

4: 1) MsCl, DMAP, pyridine, 2) NaOMe / 1) 0 deg C, 3 h, 2) MeOH, 0 deg C, 1 h

With pyridine; 2,6-dimethylpyridine; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; sodium methylate; methanesulfonyl chloride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo951646q

Reference yield:

: 143347-68-6
(1R,4R,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-oxa-bicyclo[3.2.1]octan-7-one

: 176656-10-3
(R)-2-{(E)-(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-[(1R,3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexyl]-1,3-dimethyl-but-3-enyl}-oxirane

Guidance literature:: Multi-step reaction with 10 steps

1: 1) Mg, Et₃N / 1) toluene, 25 deg C, 2) temperature below 5 deg C

2: 91 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 48 h / 25 °C

3: 78 percent / 1) KHMDS, HMPA / tetrahydrofuran / 1) -10 deg C -> 0 deg C, 1 h, 2) -78 deg C -> 25 deg C; 25 deg C, 12 h

4: 98 percent / K₂CO₃ / tetrahydrofuran / 12 h

7: 2,6-lutidine / CH₂Cl₂ / 12 h / 0 °C

8: NMO, OsO₄ / tetrahydrofuran / 1) 0 deg C -> 15 deg C, 10 h, 2) 25 deg C, 17 h

9: 93 percent / pyridine, DMAP / 0.5 h

10: 1) MsCl, DMAP, pyridine, 2) NaOMe / 1) 0 deg C, 3 h, 2) MeOH, 0 deg C, 1 h

With pyridine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; 2,6-di-tert-butyl-4-methylpyridine; sodium methylate; potassium hexamethylsilazane; potassium carbonate; magnesium; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo951646q

Reference yield:

: 176656-02-3
1-[(1R,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-cyclohexyl]-propan-1-one

: 176656-10-3
(R)-2-{(E)-(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-[(1R,3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexyl]-1,3-dimethyl-but-3-enyl}-oxirane

Guidance literature:: Multi-step reaction with 9 steps

1: 91 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 48 h / 25 °C

2: 78 percent / 1) KHMDS, HMPA / tetrahydrofuran / 1) -10 deg C -> 0 deg C, 1 h, 2) -78 deg C -> 25 deg C; 25 deg C, 12 h

3: 98 percent / K₂CO₃ / tetrahydrofuran / 12 h

6: 2,6-lutidine / CH₂Cl₂ / 12 h / 0 °C

7: NMO, OsO₄ / tetrahydrofuran / 1) 0 deg C -> 15 deg C, 10 h, 2) 25 deg C, 17 h

8: 93 percent / pyridine, DMAP / 0.5 h

9: 1) MsCl, DMAP, pyridine, 2) NaOMe / 1) 0 deg C, 3 h, 2) MeOH, 0 deg C, 1 h

With pyridine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; 2,6-di-tert-butyl-4-methylpyridine; sodium methylate; potassium hexamethylsilazane; potassium carbonate; methanesulfonyl chloride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo951646q