(5S,9S)-8-(Z)-benzylidene-2-((1S,2R)-(Z)-1,2-epoxyhex-3-enyl)-3-methyl-9-triisopropylsiloxy-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

Base Information

• Chemical Name: (5S,9S)-8-(Z)-benzylidene-2-((1S,2R)-(Z)-1,2-epoxyhex-3-enyl)-3-methyl-9-triisopropylsiloxy-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
• CAS No.: 859216-24-3
• Molecular Formula: C₃₀H₄₁NO₅Si
• Molecular Weight: 523.745
• Mol file: 859216-24-3.mol

Synonyms:(5S,9S)-8-(Z)-benzylidene-2-((1S,2R)-(Z)-1,2-epoxyhex-3-enyl)-3-methyl-9-triisopropylsiloxy-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

Chemical Property of (5S,9S)-8-(Z)-benzylidene-2-((1S,2R)-(Z)-1,2-epoxyhex-3-enyl)-3-methyl-9-triisopropylsiloxy-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,9S)-8-(Z)-benzylidene-2-((1S,2R)-(Z)-1,2-epoxyhex-3-enyl)-3-methyl-9-triisopropylsiloxy-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

There total 4 articles about (5S,9S)-8-(Z)-benzylidene-2-((1S,2R)-(Z)-1,2-epoxyhex-3-enyl)-3-methyl-9-triisopropylsiloxy-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione 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: 47.0%

(3S,4S)-5-(Z)-benzylidene-3-((4R,5R)-(Z)-4,5-epoxy-3-hydroxy-2-methylnon-6-enoyl)-3-hydroxy-4-triisopropylsiloxypyrrolidin-2-one (859216-23-2) → (5S,9S)-8-(Z)-benzylidene-2-((1S,2R)-(Z)-1,2-epoxyhex-3-enyl)-3-methyl-9-triisopropylsiloxy-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione (859216-24-3)

Guidance literature:

With water; sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jo050664x

Reference yield:

(2R,3R)-(Z)-2,3-epoxy-hept-4-en-1-ol (859216-22-1) → (5S,9S)-8-(Z)-benzylidene-2-((1S,2R)-(Z)-1,2-epoxyhex-3-enyl)-3-methyl-9-triisopropylsiloxy-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione (859216-24-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 93 percent / NEt₃; SO₃*py / CH₂Cl₂; dimethylsulfoxide / 1 h / 0 °C

2.1: LDA; HMPA / tetrahydrofuran; hexane / 1.5 h / -78 °C

2.2: 45 percent / tetrahydrofuran; hexane / 1 h / -50 °C

3.1: 47 percent / NaHCO₃; Dess-Martin periodinane; H₂O / CH₂Cl₂ / 0 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; pyridine-SO₃ complex; water; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/jo050664x

Reference yield:

(2S,3R)-(Z)-2,3-epoxy-hept-4-enal (859216-17-4) → (5S,9S)-8-(Z)-benzylidene-2-((1S,2R)-(Z)-1,2-epoxyhex-3-enyl)-3-methyl-9-triisopropylsiloxy-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione (859216-24-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LDA; HMPA / tetrahydrofuran; hexane / 1.5 h / -78 °C

1.2: 45 percent / tetrahydrofuran; hexane / 1 h / -50 °C

2.1: 47 percent / NaHCO₃; Dess-Martin periodinane; H₂O / CH₂Cl₂ / 0 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; water; sodium hydrogencarbonate; Dess-Martin periodane; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jo050664x

upstream raw materials:

(3S,4S)-5-(Z)-benzylidene-3-((4R,5R)-(Z)-4,5-epoxy-3-hydroxy-2-methylnon-6-enoyl)-3-hydroxy-4-triisopropylsiloxypyrrolidin-2-one

(2S,3R)-(Z)-2,3-epoxy-hept-4-enal

(2R,3R)-(Z)-2,3-epoxy-hept-4-en-1-ol

(2R,3R)-(Z)-2,3-epoxy-4-(tert-butyldimethylsilyloxy)hept-4-ene

Downstream raw materials:

(5S,8R,9R)-2-((1S,2R)-(Z)-1,2-epoxyhex-3-enyl)-8-hydroxy-8-(hydroxy-phenyl-methyl)-3-methyl-9-triisopropylsiloxy-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

(5S,8S,9R)-8-benzoyl-2-((1S,2R)-(Z)-1,2-epoxyhex-3-enyl)-8-hydroxy-3-methyl-6,9-bis-triisopropylsiloxy-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one

(5S,8S,9R)-8-benzoyl-2-((1S,2R)-(Z)-1,2-epoxyhex-3-enyl)-8-methoxy-3-methyl-9-triisopropylsiloxy-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

(5S,8S,9R)-8-benzoyl-2-((1S,2R)-(Z)-1,2-epoxyhex-3-enyl)-8-hydroxy-3-methyl-9-triisopropylsiloxy-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione