2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2-((1S,3aS,6aS)-3a-methyl-6-methylene-1,3a,4,5,6,6a-hexahydro-pentalen-1-yl)-malonic acid diethyl ester

Base Information

Chemical Name:2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2-((1S,3aS,6aS)-3a-methyl-6-methylene-1,3a,4,5,6,6a-hexahydro-pentalen-1-yl)-malonic acid diethyl ester
CAS No.:178763-22-9
Molecular Formula:C₃₅H₄₆O₅Si
Molecular Weight:574.833
Hs Code.:

Synonyms:2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2-((1S,3aS,6aS)-3a-methyl-6-methylene-1,3a,4,5,6,6a-hexahydro-pentalen-1-yl)-malonic acid diethyl ester

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Chemical Property of 2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2-((1S,3aS,6aS)-3a-methyl-6-methylene-1,3a,4,5,6,6a-hexahydro-pentalen-1-yl)-malonic acid diethyl ester

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Technology Process of 2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2-((1S,3aS,6aS)-3a-methyl-6-methylene-1,3a,4,5,6,6a-hexahydro-pentalen-1-yl)-malonic acid diethyl ester

There total 8 articles about 2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2-((1S,3aS,6aS)-3a-methyl-6-methylene-1,3a,4,5,6,6a-hexahydro-pentalen-1-yl)-malonic acid diethyl ester 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:

: C₂₅H₃₃O₅Si^(1-)*Na⁽¹⁺⁾

: 134005-27-9
5-methyl-5-(3-trifluoromethanesulfonyloxy-3-buten-1-yl)cyclopentadiene

: 2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2-((1R,3aR,6aR)-3a-methyl-6-methylene-1,3a,4,5,6,6a-hexahydro-pentalen-1-yl)-malonic acid diethyl ester

: 178763-22-9
2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2-((1S,3aS,6aS)-3a-methyl-6-methylene-1,3a,4,5,6,6a-hexahydro-pentalen-1-yl)-malonic acid diethyl ester

Guidance literature:: With (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); sodium bromide; bis(η3-allyl-μ-chloropalladium(II)); In dimethyl sulfoxide; at 20 ℃; for 1h; Title compound not separated from byproducts.;
DOI:10.1055/s-2006-951537

Reference yield:

: 25112-78-1
2-methyl-2-(3-oxobutyl)-1,3-cyclopentanedione

: 178763-22-9
2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2-((1S,3aS,6aS)-3a-methyl-6-methylene-1,3a,4,5,6,6a-hexahydro-pentalen-1-yl)-malonic acid diethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / TMSOTf / CH₂Cl₂ / 40 h / -78 °C

2: NaBH₄ / methanol / 1 h / 0 - 20 °C

3: DMAP, pyridine / 42 h / Ambient temperature

4: DBU / toluene / 40 h / Heating

5: 94 percent / TsOH*H₂O / acetone / 48 h / Ambient temperature

6: 71 percent / LDA / tetrahydrofuran / -78 - 20 °C

7: 2, (S)-BINAP, NaBr / dimethylsulfoxide / 1 h / Ambient temperature

With pyridine; dmap; sodium tetrahydroborate; bis(η3-allyl-μ-chloropalladium(II)); trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); sodium bromide; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; acetone; toluene;
DOI:10.1021/ja9609359

Reference yield:

: 134005-26-8
5-methyl-5-(3-oxobutyl)cyclopentadiene

: 178763-22-9
2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2-((1S,3aS,6aS)-3a-methyl-6-methylene-1,3a,4,5,6,6a-hexahydro-pentalen-1-yl)-malonic acid diethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 71 percent / LDA / tetrahydrofuran / -78 - 20 °C

2: 2, (S)-BINAP, NaBr / dimethylsulfoxide / 1 h / Ambient temperature

With bis(η3-allyl-μ-chloropalladium(II)); (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); sodium bromide; lithium diisopropyl amide; In tetrahydrofuran; dimethyl sulfoxide;
DOI:10.1021/ja9609359