(1aS,2aR,5R,5aR,6R,6aR)-1a-Methyl-5-(4-methyl-pent-3-enyl)-5-phenylselanyl-6-triethylsilanyloxy-hexahydro-1,3-dioxa-cyclopropa[f]inden-4-one

Base Information

Chemical Name:(1aS,2aR,5R,5aR,6R,6aR)-1a-Methyl-5-(4-methyl-pent-3-enyl)-5-phenylselanyl-6-triethylsilanyloxy-hexahydro-1,3-dioxa-cyclopropa[f]inden-4-one
CAS No.:79802-68-9
Molecular Formula:C₂₇H₄₀O₄SeSi
Molecular Weight:535.658
Hs Code.:

Synonyms:(1aS,2aR,5R,5aR,6R,6aR)-1a-Methyl-5-(4-methyl-pent-3-enyl)-5-phenylselanyl-6-triethylsilanyloxy-hexahydro-1,3-dioxa-cyclopropa[f]inden-4-one

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Chemical Property of (1aS,2aR,5R,5aR,6R,6aR)-1a-Methyl-5-(4-methyl-pent-3-enyl)-5-phenylselanyl-6-triethylsilanyloxy-hexahydro-1,3-dioxa-cyclopropa[f]inden-4-one

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Technology Process of (1aS,2aR,5R,5aR,6R,6aR)-1a-Methyl-5-(4-methyl-pent-3-enyl)-5-phenylselanyl-6-triethylsilanyloxy-hexahydro-1,3-dioxa-cyclopropa[f]inden-4-one

There total 6 articles about (1aS,2aR,5R,5aR,6R,6aR)-1a-Methyl-5-(4-methyl-pent-3-enyl)-5-phenylselanyl-6-triethylsilanyloxy-hexahydro-1,3-dioxa-cyclopropa[f]inden-4-one 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: 72.0%

: 1666-13-3
diphenyl diselenide

: 79802-67-8
(1aR,2R,2aR,3R,5aR,6aS)-6a-Methyl-3-(4-methyl-pent-3-enyl)-2-triethylsilanyloxy-hexahydro-1,5-dioxa-cyclopropa[f]inden-4-one

: 79802-68-9
(1aS,2aR,5R,5aR,6R,6aR)-1a-Methyl-5-(4-methyl-pent-3-enyl)-5-phenylselanyl-6-triethylsilanyloxy-hexahydro-1,3-dioxa-cyclopropa[f]inden-4-one

Guidance literature:: With potassium hexamethylsilazane; 1.) THF, -100 deg C, 10 min 2.) THF-HMPTA, -100 deg C, 1.5 h, then -> -20 deg C, 1 h; -20 deg C, 45 min;
DOI:10.1021/ja00341a044

Reference yield:

: 994-30-9
triethylsilyl chloride

: 79802-68-9
(1aS,2aR,5R,5aR,6R,6aR)-1a-Methyl-5-(4-methyl-pent-3-enyl)-5-phenylselanyl-6-triethylsilanyloxy-hexahydro-1,3-dioxa-cyclopropa[f]inden-4-one

Guidance literature:: Multi-step reaction with 3 steps

1: 99.5 percent / Et₃N, dimethylaminipyridine / CH₂Cl₂ / 12 h / Ambient temperature

2: 71 percent / 1.) LDA / 1.) THF-hexane, -78 deg C, 1 h, 2.) -78 deg C,1 h; 4 deg C, 12 h

3: 72 percent / 1.) KN(TMS)2 / 1.) THF, -100 deg C, 10 min 2.) THF-HMPTA, -100 deg C, 1.5 h, then -> -20 deg C, 1 h; -20 deg C, 45 min

With dimethylaminipyridine; potassium hexamethylsilazane; triethylamine; lithium diisopropyl amide; In dichloromethane;
DOI:10.1021/ja00341a044

Reference yield:

: 79802-65-6
(1aR,2aS,5aR,6S,6aS)-6-Hydroxy-1a-methyl-hexahydro-1,3-dioxa-cyclopropa[f]inden-4-one

: 79802-68-9
(1aS,2aR,5R,5aR,6R,6aR)-1a-Methyl-5-(4-methyl-pent-3-enyl)-5-phenylselanyl-6-triethylsilanyloxy-hexahydro-1,3-dioxa-cyclopropa[f]inden-4-one

Guidance literature:: Multi-step reaction with 3 steps

1: 99.5 percent / Et₃N, dimethylaminipyridine / CH₂Cl₂ / 12 h / Ambient temperature

2: 71 percent / 1.) LDA / 1.) THF-hexane, -78 deg C, 1 h, 2.) -78 deg C,1 h; 4 deg C, 12 h

3: 72 percent / 1.) KN(TMS)2 / 1.) THF, -100 deg C, 10 min 2.) THF-HMPTA, -100 deg C, 1.5 h, then -> -20 deg C, 1 h; -20 deg C, 45 min

With dimethylaminipyridine; potassium hexamethylsilazane; triethylamine; lithium diisopropyl amide; In dichloromethane;
DOI:10.1021/ja00341a044