[8S,9S]-(5S)-(tert-butyldimethylsilanyloxy)-1-(toluene-4-sulfonyl)-4,4a,5,7a-tetrahydro-1H-cyclopenta[d][1,3]oxazin-2-one

Base Information

Chemical Name:[8S,9S]-(5S)-(tert-butyldimethylsilanyloxy)-1-(toluene-4-sulfonyl)-4,4a,5,7a-tetrahydro-1H-cyclopenta[d][1,3]oxazin-2-one
CAS No.:350987-79-0
Molecular Formula:C₂₀H₂₉NO₅SSi
Molecular Weight:423.605
Hs Code.:

Synonyms:[8S,9S]-(5S)-(tert-butyldimethylsilanyloxy)-1-(toluene-4-sulfonyl)-4,4a,5,7a-tetrahydro-1H-cyclopenta[d][1,3]oxazin-2-one

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Chemical Property of [8S,9S]-(5S)-(tert-butyldimethylsilanyloxy)-1-(toluene-4-sulfonyl)-4,4a,5,7a-tetrahydro-1H-cyclopenta[d][1,3]oxazin-2-one

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Technology Process of [8S,9S]-(5S)-(tert-butyldimethylsilanyloxy)-1-(toluene-4-sulfonyl)-4,4a,5,7a-tetrahydro-1H-cyclopenta[d][1,3]oxazin-2-one

There total 10 articles about [8S,9S]-(5S)-(tert-butyldimethylsilanyloxy)-1-(toluene-4-sulfonyl)-4,4a,5,7a-tetrahydro-1H-cyclopenta[d][1,3]oxazin-2-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: 91.0%

: 350987-78-9
[8S,9S]-(5S)-(tert-butyldimethylsilanyloxy)-(7S)-iodo-1-(toluene-4-sulfonyl)hexahydrocyclopenta[d][1,3]oxazin-2-one

: 350987-79-0
[8S,9S]-(5S)-(tert-butyldimethylsilanyloxy)-1-(toluene-4-sulfonyl)-4,4a,5,7a-tetrahydro-1H-cyclopenta[d][1,3]oxazin-2-one

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene; at 80 ℃; for 1h;
DOI:10.1021/jo015568k

Reference yield:

: 350987-66-5
(4R)-benzyl-3-((3S)-hydroxy-(2R)-vinylhex-5-enoyl)oxazolidin-2-one

: 350987-79-0
[8S,9S]-(5S)-(tert-butyldimethylsilanyloxy)-1-(toluene-4-sulfonyl)-4,4a,5,7a-tetrahydro-1H-cyclopenta[d][1,3]oxazin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

2: 92 percent / Cl₂(Cy₃P)2Ru=CHPh / CH₂Cl₂ / 2 h / Heating

3: 83.4 percent / lithium borohydride; methanol / diethyl ether; tetrahydrofuran / 3 h / 0 - 25 °C

4: 94.5 percent / tetrahydrofuran / 12 h

5: 82 percent / iodine; K₂CO₃ / diethyl ether / 36 h / 25 °C

6: 91 percent / DBU / benzene / 1 h / 80 °C

With 2,6-dimethylpyridine; methanol; lithium borohydride; iodine; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;
DOI:10.1021/jo015568k

Reference yield:

: 350987-67-6
(2R,3S)-1-[(4R)-4-benzyl-2-thioxooxazolidin-3-yl]-3-hydroxy-2-vinylhex-5-en-1-one

: 350987-79-0
[8S,9S]-(5S)-(tert-butyldimethylsilanyloxy)-1-(toluene-4-sulfonyl)-4,4a,5,7a-tetrahydro-1H-cyclopenta[d][1,3]oxazin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 70 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 °C

2: 91 percent / Cl₂(Cy₃P)2Ru=CHPh / CH₂Cl₂ / 2.5 h / Heating

3: 75 percent / lithium borohydride; methanol / diethyl ether; tetrahydrofuran / 1.5 h / 0 °C

4: 94.5 percent / tetrahydrofuran / 12 h

5: 82 percent / iodine; K₂CO₃ / diethyl ether / 36 h / 25 °C

6: 91 percent / DBU / benzene / 1 h / 80 °C

With 2,6-dimethylpyridine; methanol; lithium borohydride; iodine; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;
DOI:10.1021/jo015568k