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

Base Information

• Chemical Name: [8S,9S]-(5S)-(tert-butyldimethylsilanyloxy)-(7S)-iodo-1-(toluene-4-sulfonyl)hexahydrocyclopenta[d][1,3]oxazin-2-one
• CAS No.: 350987-78-9
• Molecular Formula: C₂₀H₃₀INO₅SSi
• Molecular Weight: 551.518

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

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

Chemical Property:

Purity/Quality:

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MSDS Files:

Useful:

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

There total 8 articles about [8S,9S]-(5S)-(tert-butyldimethylsilanyloxy)-(7S)-iodo-1-(toluene-4-sulfonyl)hexahydrocyclopenta[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:

(4R)-benzyl-3-((3S)-hydroxy-(2R)-vinylhex-5-enoyl)oxazolidin-2-one (350987-66-5) → [8S,9S]-(5S)-(tert-butyldimethylsilanyloxy)-(7S)-iodo-1-(toluene-4-sulfonyl)hexahydrocyclopenta[d][1,3]oxazin-2-one (350987-78-9)

Guidance literature:

Multi-step reaction with 5 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

With 2,6-dimethylpyridine; methanol; lithium borohydride; iodine; potassium carbonate; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo015568k

Reference yield:

(2R,3S)-1-[(4R)-4-benzyl-2-thioxooxazolidin-3-yl]-3-hydroxy-2-vinylhex-5-en-1-one (350987-67-6) → [8S,9S]-(5S)-(tert-butyldimethylsilanyloxy)-(7S)-iodo-1-(toluene-4-sulfonyl)hexahydrocyclopenta[d][1,3]oxazin-2-one (350987-78-9)

Guidance literature:

Multi-step reaction with 5 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

With 2,6-dimethylpyridine; methanol; lithium borohydride; iodine; potassium carbonate; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo015568k

Reference yield:

(4R)-benzyl-3-[(3S)-(tert-butyldimethylsilanyloxy)-(2R)-vinylhex-5-enoyl]oxazolidin-2-one (350987-69-8) → [8S,9S]-(5S)-(tert-butyldimethylsilanyloxy)-(7S)-iodo-1-(toluene-4-sulfonyl)hexahydrocyclopenta[d][1,3]oxazin-2-one (350987-78-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / Cl₂(Cy₃P)2Ru=CHPh / CH₂Cl₂ / 2 h / Heating

2: 83.4 percent / lithium borohydride; methanol / diethyl ether; tetrahydrofuran / 3 h / 0 - 25 °C

3: 94.5 percent / tetrahydrofuran / 12 h

4: 82 percent / iodine; K₂CO₃ / diethyl ether / 36 h / 25 °C

With methanol; lithium borohydride; iodine; potassium carbonate; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo015568k

upstream raw materials:

Tosyl isocyanate

[(1S,5S)-5-(tert-butyldimethylsilanyloxy)cyclopent-2-enyl]methanol

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

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

Downstream raw materials:

(3aS,4R,5R,6R,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxy-4-(2-nitro-phenylselanylmethyl)-hexahydro-cyclopentaoxazol-2-one

[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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