Acetic acid (1S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methylene-cyclobutylmethyl ester

Base Information

Chemical Name:Acetic acid (1S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methylene-cyclobutylmethyl ester
CAS No.:743477-87-4
Molecular Formula:C₂₄H₃₀O₃Si
Molecular Weight:394.586
Hs Code.:

Synonyms:Acetic acid (1S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methylene-cyclobutylmethyl ester

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Chemical Property of Acetic acid (1S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methylene-cyclobutylmethyl ester

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Technology Process of Acetic acid (1S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methylene-cyclobutylmethyl ester

There total 7 articles about Acetic acid (1S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methylene-cyclobutylmethyl 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: 68.0%

: 743477-86-3
Acetic acid (1S,2R,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-iodomethyl-cyclobutylmethyl ester

: 743477-87-4
Acetic acid (1S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methylene-cyclobutylmethyl ester

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; for 24h; Heating;
DOI:10.1021/ol0491989

Reference yield:

: 1,2-O-cyclohexylidene-trans-cis-2,3-bis(hydroxymethyl)-1-cyclobutanol

: 743477-87-4
Acetic acid (1S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methylene-cyclobutylmethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 47.3 percent / Pseudomonas cepacia lipase / 2 h / 28 °C

2: Amberlite 120 IR / methanol / 1 h / 20 °C

3: 3.0 g / pyridine / 20 °C

4: 94.4 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

5: 89 percent / BF₃*OEt₂ / CH₂Cl₂; methanol / 20 °C

6: 80 percent / Me₃P(OPh)3I / dimethylformamide / 0.5 h / 20 °C

7: 68 percent / DBU / tetrahydrofuran / 24 h / Heating

With pyridine; 1H-imidazole; Pseudomonas cepacia lipase; Amberlite 120 IR; Me₃P(OPh)3I; boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol0491989

Reference yield:

: Acetic acid (1S,2S,3S)-3-hydroxy-2-hydroxymethyl-cyclobutylmethyl ester

: 743477-87-4
Acetic acid (1S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methylene-cyclobutylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 3.0 g / pyridine / 20 °C

2: 94.4 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

3: 89 percent / BF₃*OEt₂ / CH₂Cl₂; methanol / 20 °C

4: 80 percent / Me₃P(OPh)3I / dimethylformamide / 0.5 h / 20 °C

5: 68 percent / DBU / tetrahydrofuran / 24 h / Heating

With pyridine; 1H-imidazole; Me₃P(OPh)3I; boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol0491989