(5S,8R,9R)-((1S,2R)-(Z)-1,2-epoxy-hex-3-enyl)-8-(hydroxy-phenyl-methyl)-8-methoxy-3-methyl-9-trimethylsilyloxy-1-oxa-7-azaspirop[4.4]non-2-ene-4,6-dione

Base Information

Chemical Name:(5S,8R,9R)-((1S,2R)-(Z)-1,2-epoxy-hex-3-enyl)-8-(hydroxy-phenyl-methyl)-8-methoxy-3-methyl-9-trimethylsilyloxy-1-oxa-7-azaspirop[4.4]non-2-ene-4,6-dione
CAS No.:859216-46-9
Molecular Formula:C₂₅H₃₃NO₇Si
Molecular Weight:487.625
Hs Code.:

Synonyms:(5S,8R,9R)-((1S,2R)-(Z)-1,2-epoxy-hex-3-enyl)-8-(hydroxy-phenyl-methyl)-8-methoxy-3-methyl-9-trimethylsilyloxy-1-oxa-7-azaspirop[4.4]non-2-ene-4,6-dione

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Chemical Property of (5S,8R,9R)-((1S,2R)-(Z)-1,2-epoxy-hex-3-enyl)-8-(hydroxy-phenyl-methyl)-8-methoxy-3-methyl-9-trimethylsilyloxy-1-oxa-7-azaspirop[4.4]non-2-ene-4,6-dione

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Technology Process of (5S,8R,9R)-((1S,2R)-(Z)-1,2-epoxy-hex-3-enyl)-8-(hydroxy-phenyl-methyl)-8-methoxy-3-methyl-9-trimethylsilyloxy-1-oxa-7-azaspirop[4.4]non-2-ene-4,6-dione

There total 8 articles about (5S,8R,9R)-((1S,2R)-(Z)-1,2-epoxy-hex-3-enyl)-8-(hydroxy-phenyl-methyl)-8-methoxy-3-methyl-9-trimethylsilyloxy-1-oxa-7-azaspirop[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: 65.0%

: 859216-45-8
(5S,9S)-8-(Z)-benzylidene-2-((1S,2R)-(Z)-1,2-epoxy-hex-3-enyl)-3-methyl-9-trimethylsilyloxy-1-oxa-7-azaspirop[4.4]non-2-ene-4,6-dione

: 67-56-1
methanol

: 859216-46-9
(5S,8R,9R)-((1S,2R)-(Z)-1,2-epoxy-hex-3-enyl)-8-(hydroxy-phenyl-methyl)-8-methoxy-3-methyl-9-trimethylsilyloxy-1-oxa-7-azaspirop[4.4]non-2-ene-4,6-dione

: (5S,8R,9R)-2-[(2S,3R)-((Z)-3-But-1-enyl)-oxiranyl]-8-hydroxy-8-(hydroxy-phenyl-methyl)-3-methyl-9-trimethylsilanyloxy-1-oxa-7-aza-spiro[4.4]non-2-ene-4,6-dione

Guidance literature:: With 3 A molecular sieve; 3,3-dimethyldioxirane; In acetone; at -60 ℃; for 4h;
DOI:10.1021/jo050664x

Reference yield:

: 859216-17-4
(2S,3R)-(Z)-2,3-epoxy-hept-4-enal

: 859216-46-9
(5S,8R,9R)-((1S,2R)-(Z)-1,2-epoxy-hex-3-enyl)-8-(hydroxy-phenyl-methyl)-8-methoxy-3-methyl-9-trimethylsilyloxy-1-oxa-7-azaspirop[4.4]non-2-ene-4,6-dione

Guidance literature:: Multi-step reaction with 3 steps

1.1: LDA; HMPA / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 32 percent / tetrahydrofuran; hexane / 1 h / -78 - -50 °C

2.1: 52 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂; H₂O / 0.05 h / 20 °C

3.1: 65 percent / molecular sieves 3 Angstroem; dimethyl dioxirane / acetone / 4 h / -60 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; 3 A molecular sieve; 3,3-dimethyldioxirane; sodium hydrogencarbonate; Dess-Martin periodane; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; water; acetone;
DOI:10.1021/jo050664x

Reference yield:

: 859216-22-1
(2R,3R)-(Z)-2,3-epoxy-hept-4-en-1-ol

: 859216-46-9
(5S,8R,9R)-((1S,2R)-(Z)-1,2-epoxy-hex-3-enyl)-8-(hydroxy-phenyl-methyl)-8-methoxy-3-methyl-9-trimethylsilyloxy-1-oxa-7-azaspirop[4.4]non-2-ene-4,6-dione

Guidance literature:: Multi-step reaction with 4 steps

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

2.1: LDA; HMPA / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: 32 percent / tetrahydrofuran; hexane / 1 h / -78 - -50 °C

3.1: 52 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂; H₂O / 0.05 h / 20 °C

4.1: 65 percent / molecular sieves 3 Angstroem; dimethyl dioxirane / acetone / 4 h / -60 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; pyridine-SO₃ complex; 3 A molecular sieve; 3,3-dimethyldioxirane; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; water; dimethyl sulfoxide; acetone;
DOI:10.1021/jo050664x