Ethyl (E)-4-[2,2-dimethyl-5-(toluene-4-sulfonyl)tetrahydro[1,3]dioxolo[4,5-c]pyrrol-4-yl]-4-triisopropylsilyloxy-2-butenoate

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Chemical Name:Ethyl (E)-4-[2,2-dimethyl-5-(toluene-4-sulfonyl)tetrahydro[1,3]dioxolo[4,5-c]pyrrol-4-yl]-4-triisopropylsilyloxy-2-butenoate
CAS No.:253778-07-3
Molecular Formula:C₂₉H₄₇NO₇SSi
Molecular Weight:581.846
Hs Code.:

Synonyms:Ethyl (E)-4-[2,2-dimethyl-5-(toluene-4-sulfonyl)tetrahydro[1,3]dioxolo[4,5-c]pyrrol-4-yl]-4-triisopropylsilyloxy-2-butenoate

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Chemical Property of Ethyl (E)-4-[2,2-dimethyl-5-(toluene-4-sulfonyl)tetrahydro[1,3]dioxolo[4,5-c]pyrrol-4-yl]-4-triisopropylsilyloxy-2-butenoate

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Technology Process of Ethyl (E)-4-[2,2-dimethyl-5-(toluene-4-sulfonyl)tetrahydro[1,3]dioxolo[4,5-c]pyrrol-4-yl]-4-triisopropylsilyloxy-2-butenoate

There total 3 articles about Ethyl (E)-4-[2,2-dimethyl-5-(toluene-4-sulfonyl)tetrahydro[1,3]dioxolo[4,5-c]pyrrol-4-yl]-4-triisopropylsilyloxy-2-butenoate 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: 90.0%

: 867-13-0
diethoxyphosphoryl-acetic acid ethyl ester

: 253778-04-0
[2,2-Dimethyl-5-(toluene-4-sulfonyl)tetrahydro[1,3]dioxolo[4,5-c]pyrrol-4-yl]-2-triisopropylsilyloxyacetaldehyde

: 253778-07-3
Ethyl (E)-4-[2,2-dimethyl-5-(toluene-4-sulfonyl)tetrahydro[1,3]dioxolo[4,5-c]pyrrol-4-yl]-4-triisopropylsilyloxy-2-butenoate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In acetonitrile; at 20 ℃; for 2h;
DOI:10.1002/(SICI)1521-3765(19991105)5:11<3279::AID-CHEM3279>3.0.CO;2-4

Reference yield:

: 253778-03-9
2-[2,2-Dimethyl-5-(toluene-4-sulfonyl)tetrahydro[1,3]dioxolo[4,5-c]pyrrol-4-yl]-2-triisopropylsilyloxyethanol

: 253778-07-3
Ethyl (E)-4-[2,2-dimethyl-5-(toluene-4-sulfonyl)tetrahydro[1,3]dioxolo[4,5-c]pyrrol-4-yl]-4-triisopropylsilyloxy-2-butenoate

Guidance literature:: Multi-step reaction with 2 steps

1: 98 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.75 h / 20 °C

2: 90 percent / LiCl; DBU / acetonitrile / 2 h / 20 °C

With sodium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In dichloromethane; acetonitrile; 1: Oxidation / 2: Condensation;
DOI:10.1002/(SICI)1521-3765(19991105)5:11<3279::AID-CHEM3279>3.0.CO;2-4

Reference yield:

: 253778-02-8
N-[3-Hydroxy-1-(5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-triisopropylsilyloxypropyl]-4-methylbenzenesulfonamide

: 253778-07-3
Ethyl (E)-4-[2,2-dimethyl-5-(toluene-4-sulfonyl)tetrahydro[1,3]dioxolo[4,5-c]pyrrol-4-yl]-4-triisopropylsilyloxy-2-butenoate

Guidance literature:: Multi-step reaction with 3 steps

1: 86 percent / PPh₃; DIAD / tetrahydrofuran / 0.75 h / 0 °C

2: 98 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.75 h / 20 °C

3: 90 percent / LiCl; DBU / acetonitrile / 2 h / 20 °C

With di-isopropyl azodicarboxylate; sodium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; lithium chloride; In tetrahydrofuran; dichloromethane; acetonitrile; 1: Cyclization / 2: Oxidation / 3: Condensation;
DOI:10.1002/(SICI)1521-3765(19991105)5:11<3279::AID-CHEM3279>3.0.CO;2-4