1-[2,2-Dimethyl-5-(toluene-4-sulfonyl)tetrahydro[1,3]dioxolo[4,5-c]pyrrol-4-yl]-1-triisopropylsilyloxybut-3-en-2-ol

Base Information

Chemical Name:1-[2,2-Dimethyl-5-(toluene-4-sulfonyl)tetrahydro[1,3]dioxolo[4,5-c]pyrrol-4-yl]-1-triisopropylsilyloxybut-3-en-2-ol
CAS No.:253778-05-1
Molecular Formula:C₂₇H₄₅NO₆SSi
Molecular Weight:539.809
Hs Code.:

Synonyms:1-[2,2-Dimethyl-5-(toluene-4-sulfonyl)tetrahydro[1,3]dioxolo[4,5-c]pyrrol-4-yl]-1-triisopropylsilyloxybut-3-en-2-ol

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Chemical Property of 1-[2,2-Dimethyl-5-(toluene-4-sulfonyl)tetrahydro[1,3]dioxolo[4,5-c]pyrrol-4-yl]-1-triisopropylsilyloxybut-3-en-2-ol

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Technology Process of 1-[2,2-Dimethyl-5-(toluene-4-sulfonyl)tetrahydro[1,3]dioxolo[4,5-c]pyrrol-4-yl]-1-triisopropylsilyloxybut-3-en-2-ol

There total 3 articles about 1-[2,2-Dimethyl-5-(toluene-4-sulfonyl)tetrahydro[1,3]dioxolo[4,5-c]pyrrol-4-yl]-1-triisopropylsilyloxybut-3-en-2-ol 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: 95.0%

: 1826-67-1
vinyl magnesium bromide

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

: 253778-05-1
1-[2,2-Dimethyl-5-(toluene-4-sulfonyl)tetrahydro[1,3]dioxolo[4,5-c]pyrrol-4-yl]-1-triisopropylsilyloxybut-3-en-2-ol

Guidance literature:: In tetrahydrofuran; at -78 ℃; for 0.166667h;
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

: 253778-05-1
1-[2,2-Dimethyl-5-(toluene-4-sulfonyl)tetrahydro[1,3]dioxolo[4,5-c]pyrrol-4-yl]-1-triisopropylsilyloxybut-3-en-2-ol

Guidance literature:: Multi-step reaction with 2 steps

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

2: 95 percent / tetrahydrofuran / 0.17 h / -78 °C

With sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 1: Oxidation / 2: Grignard reaction;
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

: 253778-05-1
1-[2,2-Dimethyl-5-(toluene-4-sulfonyl)tetrahydro[1,3]dioxolo[4,5-c]pyrrol-4-yl]-1-triisopropylsilyloxybut-3-en-2-ol

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: 95 percent / tetrahydrofuran / 0.17 h / -78 °C

With di-isopropyl azodicarboxylate; sodium hydrogencarbonate; Dess-Martin periodane; triphenylphosphine; In tetrahydrofuran; dichloromethane; 1: Cyclization / 2: Oxidation / 3: Grignard reaction;
DOI:10.1002/(SICI)1521-3765(19991105)5:11<3279::AID-CHEM3279>3.0.CO;2-4