1-Oxa-7-azaspiro[4.4]non-2-ene-4,6-dione,8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexen-1-yl]-8,9-dihydroxy-3-methyl-,(5S,8S,9R)-

Base Information

Chemical Name:1-Oxa-7-azaspiro[4.4]non-2-ene-4,6-dione,8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexen-1-yl]-8,9-dihydroxy-3-methyl-,(5S,8S,9R)-
CAS No.:149883-42-1
Molecular Formula:C21H23 N O8
Molecular Weight:417.416
Hs Code.:
Mol file:149883-42-1.mol

Synonyms:1-Oxa-7-azaspiro[4.4]non-2-ene-4,6-dione,8-benzoyl-2-(1,2-dihydroxy-3-hexenyl)-8,9-dihydroxy-3-methyl-, [5S-[5a(1R*,2R*,3Z),8b,9b]]-; 1-Oxa-7-azaspiro[4.4]non-2-ene-4,6-dione,8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexenyl]-8,9-dihydroxy-3-methyl-,(5S,8S,9R)- (9CI); Pseurotin F2

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Chemical Property of 1-Oxa-7-azaspiro[4.4]non-2-ene-4,6-dione,8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexen-1-yl]-8,9-dihydroxy-3-methyl-,(5S,8S,9R)-

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MSDS Files:: SDS file from LookChem

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Technology Process of 1-Oxa-7-azaspiro[4.4]non-2-ene-4,6-dione,8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexen-1-yl]-8,9-dihydroxy-3-methyl-,(5S,8S,9R)-

There total 39 articles about 1-Oxa-7-azaspiro[4.4]non-2-ene-4,6-dione,8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexen-1-yl]-8,9-dihydroxy-3-methyl-,(5S,8S,9R)- 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: 89.0%

: 660842-22-8
(5S,8S,9R)-8-benzoyl-2-[(1S,2S,3Z)-1,2-bis(methoxymethoxy)-3-hexenyl]-8-hydroxy-9-methoxymethoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

: 149883-42-1
(5S,8S,9R)-8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexenyl]-8,9-dihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

Guidance literature:: With hydrogenchloride; In methanol; at 20 ℃; for 8h;
DOI:10.1246/bcsj.77.1703

Reference yield: 67.0%

: 67-56-1
methanol

: 562858-39-3
(5S,8S,9R)-8-benzoyl-2-((2S,4S,5S)-(Z)-5-(but-1-enyl)-2-methyl-[1,3]dioxolan-4-yl)-8,9-dihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

: 58523-30-1
pseurotin A

: 149883-42-1
(5S,8S,9R)-8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexenyl]-8,9-dihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

Guidance literature:: With acetyl chloride; In methanol; at 20 ℃; for 11h;
DOI:10.1021/ol034630s

Reference yield:

: 499120-97-7
(2S,3R,4R)-4-benzyloxy-2,3-isopropylidenedioxy-3-vinyl-hexan-1-ol

: 149883-42-1
(5S,8S,9R)-8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexenyl]-8,9-dihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

Guidance literature:: Multi-step reaction with 21 steps

1.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

2.1: 14 percent / tetrahydrofuran / 20 °C

3.1: O₃ / CH₂Cl₂ / 1 h / -78 °C

3.2: Ph₃P / CH₂Cl₂ / 1.5 h / -78 - 20 °C

4.1: aq. CF₃CO₂H / 9 h / 20 °C

5.1: 1.11 g / N-iodosuccinimide; n-Bu₄NI / CH₂Cl₂ / 72 h / 20 °C

6.1: 95 percent / pyridine / 12 h / 50 °C

7.1: 94 percent / H₂ / Pd/C / ethanol / 72 h

8.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 9 h / 20 °C

9.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C

9.2: tetrahydrofuran; toluene / 1 h / -78 °C

10.1: HF*pyridine; pyridine / 2.5 h / 20 °C

11.1: 23.6 mg / Dess-Martin periodinane / CH₂Cl₂ / 6 h / 20 °C

12.1: 97 percent / thionyl chloride; pyridine / 0.17 h / 0 °C

13.1: HF*pyridine; pyridine / 3 h / 20 °C

14.1: 131 mg / P₂O₅ / CH₂Cl₂ / 1.5 h / 0 °C

15.1: NH₃ / propan-2-ol / 3 h / 20 °C

16.1: Dess-Martin periodinane / CH₂Cl₂ / 6 h / 20 °C

17.1: 110 mg / aq. Na₂CO₃ / 10 h

18.1: AcOH / propan-2-ol / 66 h / 70 °C

19.1: m-CPBA / CH₂Cl₂ / 5 h / 20 °C

19.2: aq. Na₂SO₃

20.1: 9.3 mg / Dess-Martin periodinane / CH₂Cl₂ / 11 h / 20 °C

21.1: 89 percent / aq. HCl / methanol / 8 h / 20 °C

With pyridine; hydrogenchloride; N-iodo-succinimide; thionyl chloride; ammonia; hydrogen; phosphorus pentoxide; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium carbonate; Dess-Martin periodane; pyridine hydrogenfluoride; ozone; acetic acid; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; isopropyl alcohol; toluene; 1.1: Dess-Martin oxidation / 8.1: Dess-Martin oxidation / 11.1: Dess-Martin oxidation / 16.1: Dess-Martin oxidation / 20.1: Dess-Martin oxidation;
DOI:10.1246/bcsj.77.1703