(1S,7aS)-1-((Z)-(R)-6-Benzyloxy-4-methyl-2-trimethylsilanyl-hex-2-enyl)-1-methyl-tetrahydro-pyrrolo[1,2-c]oxazole

Base Information

Chemical Name:(1S,7aS)-1-((Z)-(R)-6-Benzyloxy-4-methyl-2-trimethylsilanyl-hex-2-enyl)-1-methyl-tetrahydro-pyrrolo[1,2-c]oxazole
CAS No.:90246-46-1
Molecular Formula:C₂₄H₃₉NO₂Si
Molecular Weight:401.665
Hs Code.:

Synonyms:(1S,7aS)-1-((Z)-(R)-6-Benzyloxy-4-methyl-2-trimethylsilanyl-hex-2-enyl)-1-methyl-tetrahydro-pyrrolo[1,2-c]oxazole

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Chemical Property of (1S,7aS)-1-((Z)-(R)-6-Benzyloxy-4-methyl-2-trimethylsilanyl-hex-2-enyl)-1-methyl-tetrahydro-pyrrolo[1,2-c]oxazole

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Technology Process of (1S,7aS)-1-((Z)-(R)-6-Benzyloxy-4-methyl-2-trimethylsilanyl-hex-2-enyl)-1-methyl-tetrahydro-pyrrolo[1,2-c]oxazole

There total 16 articles about (1S,7aS)-1-((Z)-(R)-6-Benzyloxy-4-methyl-2-trimethylsilanyl-hex-2-enyl)-1-methyl-tetrahydro-pyrrolo[1,2-c]oxazole 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:

: chloroformate ester of 5-(benzyloxy)-1-pentyn-3-ol

: 90246-46-1
(1S,7aS)-1-((Z)-(R)-6-Benzyloxy-4-methyl-2-trimethylsilanyl-hex-2-enyl)-1-methyl-tetrahydro-pyrrolo[1,2-c]oxazole

Guidance literature:: Multi-step reaction with 8 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

With pyridine; dmap; potassium hydroxide; copper(l) iodide; trichlorosilane; methyllithium; diisobutylaluminium hydride; In methanol; diethyl ether; ethanol; water;
DOI:10.1021/ja00327a022

Reference yield:

: 51207-68-2
(2S)-N-Benzyloxycarbony-2-(1'-hydroxy-1'-methylethyl)pyrrolidine

: 90246-46-1
(1S,7aS)-1-((Z)-(R)-6-Benzyloxy-4-methyl-2-trimethylsilanyl-hex-2-enyl)-1-methyl-tetrahydro-pyrrolo[1,2-c]oxazole

Guidance literature:: Multi-step reaction with 5 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

With potassium hydroxide; thionyl chloride; methyllithium; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water;
DOI:10.1021/ja00327a022

Reference yield:

: 51207-70-6
(2S)-N-Benzyloxycarbony-2-(1'-methylethenyl)pyrrolidine

: 90246-46-1
(1S,7aS)-1-((Z)-(R)-6-Benzyloxy-4-methyl-2-trimethylsilanyl-hex-2-enyl)-1-methyl-tetrahydro-pyrrolo[1,2-c]oxazole

Guidance literature:: Multi-step reaction with 4 steps

1: 37 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 3 h / 25 °C

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

3: KOH / ethanol / 12 h / 90 °C

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

With potassium hydroxide; methyllithium; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; In methanol; ethanol; dichloromethane; water;
DOI:10.1021/ja00327a022