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

Base Information

• Chemical Name: (1aR,2aR,5R,5aR,6R,6aR)-1a-(tert-Butyl-dimethyl-silanyloxymethyl)-5-(4-methyl-pent-3-enyl)-5-phenylselanyl-6-triethylsilanyloxy-hexahydro-1,3-dioxa-cyclopropa[f]inden-4-one
• CAS No.: 84011-81-4
• Molecular Formula: C₃₃H₅₄O₅SeSi₂
• Molecular Weight: 665.92

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

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

There total 11 articles about (1aR,2aR,5R,5aR,6R,6aR)-1a-(tert-Butyl-dimethyl-silanyloxymethyl)-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:

5-iodo-2-methylpent-2-ene (43161-11-1) → (1aR,2aR,5R,5aR,6R,6aR)-1a-(tert-Butyl-dimethyl-silanyloxymethyl)-5-(4-methyl-pent-3-enyl)-5-phenylselanyl-6-triethylsilanyloxy-hexahydro-1,3-dioxa-cyclopropa[f]inden-4-one (84011-81-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / 1.) LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 1 h, 2.) -78 deg C, 1 h; 4 deg C, overnight

2: 82 percent Turnov_. / 1.) KN(TMS)2 / 1.) THF, -100 deg C, 10 min, 2.) THF-HMPTA, -100 deg C , 1.5 h; -100 deg C -> -20 deg C, 1 h; -20 deg C 45 min

With potassium hexamethylsilazane; lithium diisopropyl amide; In tetrahydrofuran; hexane;

DOI:10.1021/ja00341a044

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (1aR,2aR,5R,5aR,6R,6aR)-1a-(tert-Butyl-dimethyl-silanyloxymethyl)-5-(4-methyl-pent-3-enyl)-5-phenylselanyl-6-triethylsilanyloxy-hexahydro-1,3-dioxa-cyclopropa[f]inden-4-one (84011-81-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 87 percent / Et₃N, dimethylaminopyridine / CH₂Cl₂ / 25 °C

2: 90 percent / benzene / 3.5 h / Irradiation

3: 97 percent / 1.) n-BuLi, tetramethylpiperidine, 2.) Et₃N / 1.) THF-hexane, 0 deg C -> RT; RT, 45 min, 2.) RT, 3 h

4: 13 percent / Pd(OAc)2, p-benzoquinone / acetonitrile / 21 h

5: 91 percent / CeCl₃, NaBH₄ / methanol / 0.17 h / 0 °C

6: 91 percent / pyridinium p-toluenesulfonate / butan-2-one / 0.17 h / Heating

7: 74 percent / NaHCO₃, MCPBA / CH₂Cl₂ / 18 h / 5 °C

8: 81 percent / Et₃N, dimethylaminopyridine / CH₂Cl₂ / 1.5 h / Heating

9: 72 percent / 1.) LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 1 h, 2.) -78 deg C, 1 h; 4 deg C, overnight

10: 82 percent Turnov_. / 1.) KN(TMS)2 / 1.) THF, -100 deg C, 10 min, 2.) THF-HMPTA, -100 deg C , 1.5 h; -100 deg C -> -20 deg C, 1 h; -20 deg C 45 min

With dmap; palladium diacetate; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; tetramethylpiperidine; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile; butanone; benzene;

DOI:10.1021/ja00341a044

Reference yield:

rel-(3aR,4S,5S,6S,7aS)-6-(t-butyldimethylsilyloxymethyl)-5,6-epoxy-4-hydroxybenzofuran-2(3H)-one (84011-63-2) → (1aR,2aR,5R,5aR,6R,6aR)-1a-(tert-Butyl-dimethyl-silanyloxymethyl)-5-(4-methyl-pent-3-enyl)-5-phenylselanyl-6-triethylsilanyloxy-hexahydro-1,3-dioxa-cyclopropa[f]inden-4-one (84011-81-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / Et₃N, dimethylaminopyridine / CH₂Cl₂ / 1.5 h / Heating

2: 72 percent / 1.) LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 1 h, 2.) -78 deg C, 1 h; 4 deg C, overnight

3: 82 percent Turnov_. / 1.) KN(TMS)2 / 1.) THF, -100 deg C, 10 min, 2.) THF-HMPTA, -100 deg C , 1.5 h; -100 deg C -> -20 deg C, 1 h; -20 deg C 45 min

With dmap; potassium hexamethylsilazane; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/ja00341a044

upstream raw materials:

diphenyl diselenide

(1aR,2R,2aR,3R,5aR,6aR)-6a-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(4-methyl-pent-3-enyl)-2-triethylsilanyloxy-hexahydro-1,5-dioxa-cyclopropa[f]inden-4-one

5-iodo-2-methylpent-2-ene

tert-butyldimethylsilyl chloride

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