1-Oxa-7-azaspiro[4.4]non-2-ene-4,6-dione, 8-benzoyl-2-[(1S,2S,3Z)-1,2-bis(methoxymethoxy)-3-hexenyl]-8-hydroxy -9-(methoxymethoxy)-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-bis(methoxymethoxy)-3-hexenyl]-8-hydroxy -9-(methoxymethoxy)-3-methyl-, (5S,8S,9R)-
CAS No.:660842-22-8
Molecular Formula:C27H35NO11
Molecular Weight:549.575
Hs Code.:

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

Synonyms:

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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-bis(methoxymethoxy)-3-hexenyl]-8-hydroxy -9-(methoxymethoxy)-3-methyl-, (5S,8S,9R)-

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:: SDS file from LookChem

Useful:

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

There total 34 articles about 1-Oxa-7-azaspiro[4.4]non-2-ene-4,6-dione, 8-benzoyl-2-[(1S,2S,3Z)-1,2-bis(methoxymethoxy)-3-hexenyl]-8-hydroxy -9-(methoxymethoxy)-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:

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

: 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

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 11h;
DOI:10.1246/bcsj.77.1703

Reference yield:

: 64638-65-9
5,6-dideoxy-1,2-O-isopropylidene-α-D-erythro-hexofuranos-3-ulose

: 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

Guidance literature:: Multi-step reaction with 28 steps

1.1: tetrahydrofuran / 1 h / -18 °C

2.1: aq. AcOH / 11 h / 80 °C

3.1: 5.60 g / N-iodosuccinimide; n-Bu₄NI / CH₂Cl₂ / 20 h / 20 °C

4.1: 79 percent / CSA / acetone / 6 h / 40 °C / 225.02 Torr

5.1: 91 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

6.1: DMAP; pyridine / 4 h / Heating

7.1: NaH / dimethylformamide / 8 h / 20 °C

8.1: 6.59 g / CSA / methanol / 48 h / 20 °C

9.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

10.1: 14 percent / tetrahydrofuran / 20 °C

11.1: O₃ / CH₂Cl₂ / 1 h / -78 °C

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

12.1: aq. CF₃CO₂H / 9 h / 20 °C

13.1: 1.11 g / N-iodosuccinimide; n-Bu₄NI / CH₂Cl₂ / 72 h / 20 °C

14.1: 95 percent / pyridine / 12 h / 50 °C

15.1: 94 percent / H₂ / Pd/C / ethanol / 72 h

16.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 9 h / 20 °C

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

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

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

19.1: 23.6 mg / Dess-Martin periodinane / CH₂Cl₂ / 6 h / 20 °C

20.1: 97 percent / thionyl chloride; pyridine / 0.17 h / 0 °C

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

22.1: 131 mg / P₂O₅ / CH₂Cl₂ / 1.5 h / 0 °C

23.1: NH₃ / propan-2-ol / 3 h / 20 °C

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

25.1: 110 mg / aq. Na₂CO₃ / 10 h

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

27.1: m-CPBA / CH₂Cl₂ / 5 h / 20 °C

27.2: aq. Na₂SO₃

28.1: 9.3 mg / Dess-Martin periodinane / CH₂Cl₂ / 11 h / 20 °C

With pyridine; dmap; N-iodo-succinimide; lithium aluminium tetrahydride; thionyl chloride; camphor-10-sulfonic acid; ammonia; hydrogen; phosphorus pentoxide; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; 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; N,N-dimethyl-formamide; isopropyl alcohol; acetone; toluene; 9.1: Dess-Martin oxidation / 16.1: Dess-Martin oxidation / 19.1: Dess-Martin oxidation / 24.1: Dess-Martin oxidation / 28.1: Dess-Martin oxidation;
DOI:10.1246/bcsj.77.1703

Reference yield:

: 16749-42-1
5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose

: 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

Guidance literature:: Multi-step reaction with 29 steps

1.1: pyridinium chlorochromate; molecular sieves 4 Angstroem / CH₂Cl₂ / 10 h / 20 °C

2.1: tetrahydrofuran / 1 h / -18 °C

3.1: aq. AcOH / 11 h / 80 °C

4.1: 5.60 g / N-iodosuccinimide; n-Bu₄NI / CH₂Cl₂ / 20 h / 20 °C

5.1: 79 percent / CSA / acetone / 6 h / 40 °C / 225.02 Torr

6.1: 91 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

7.1: DMAP; pyridine / 4 h / Heating

8.1: NaH / dimethylformamide / 8 h / 20 °C

9.1: 6.59 g / CSA / methanol / 48 h / 20 °C

10.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

11.1: 14 percent / tetrahydrofuran / 20 °C

12.1: O₃ / CH₂Cl₂ / 1 h / -78 °C

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

13.1: aq. CF₃CO₂H / 9 h / 20 °C

14.1: 1.11 g / N-iodosuccinimide; n-Bu₄NI / CH₂Cl₂ / 72 h / 20 °C

15.1: 95 percent / pyridine / 12 h / 50 °C

16.1: 94 percent / H₂ / Pd/C / ethanol / 72 h

17.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 9 h / 20 °C

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

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

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

20.1: 23.6 mg / Dess-Martin periodinane / CH₂Cl₂ / 6 h / 20 °C

21.1: 97 percent / thionyl chloride; pyridine / 0.17 h / 0 °C

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

23.1: 131 mg / P₂O₅ / CH₂Cl₂ / 1.5 h / 0 °C

24.1: NH₃ / propan-2-ol / 3 h / 20 °C

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

26.1: 110 mg / aq. Na₂CO₃ / 10 h

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

28.1: m-CPBA / CH₂Cl₂ / 5 h / 20 °C

28.2: aq. Na₂SO₃

29.1: 9.3 mg / Dess-Martin periodinane / CH₂Cl₂ / 11 h / 20 °C

With pyridine; dmap; N-iodo-succinimide; lithium aluminium tetrahydride; thionyl chloride; 4 A molecular sieve; camphor-10-sulfonic acid; ammonia; hydrogen; phosphorus pentoxide; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; sodium carbonate; Dess-Martin periodane; pyridine hydrogenfluoride; ozone; acetic acid; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; acetone; toluene; 10.1: Dess-Martin oxidation / 17.1: Dess-Martin oxidation / 20.1: Dess-Martin oxidation / 25.1: Dess-Martin oxidation / 29.1: Dess-Martin oxidation;
DOI:10.1246/bcsj.77.1703