(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

Base Information

Chemical Name:(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
CAS No.:859216-27-6
Molecular Formula:C₃₉H₆₁NO₇Si₂
Molecular Weight:712.087
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 7 articles about (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 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:

: 859216-26-5
(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

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 859216-27-6
(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

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1021/jo050664x

Reference yield:

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

: 859216-27-6
(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

Guidance literature:: Multi-step reaction with 5 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

3.1: 40 percent / dimethyl dioxirane / methanol; acetone / 16 h / -60 °C

4.1: 95 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 0.08 h / 0 °C

5.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; water; 3,3-dimethyldioxirane; sodium hydrogencarbonate; Dess-Martin periodane; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; acetone;
DOI:10.1021/jo050664x

Reference yield:

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

: 859216-27-6
(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

Guidance literature:: Multi-step reaction with 6 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

4.1: 40 percent / dimethyl dioxirane / methanol; acetone / 16 h / -60 °C

5.1: 95 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 0.08 h / 0 °C

6.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; pyridine-SO₃ complex; water; 3,3-dimethyldioxirane; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; acetone;
DOI:10.1021/jo050664x