(5S,8R,9R)-8-benzyl-2-[(1E,3E)-hexa-1,3-dienyl]-8-hydroxy-9-methoxymethoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

Base Information

Chemical Name:(5S,8R,9R)-8-benzyl-2-[(1E,3E)-hexa-1,3-dienyl]-8-hydroxy-9-methoxymethoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
CAS No.:660842-28-4
Molecular Formula:C₂₃H₂₇NO₆
Molecular Weight:413.47
Hs Code.:

Synonyms:(5S,8R,9R)-8-benzyl-2-[(1E,3E)-hexa-1,3-dienyl]-8-hydroxy-9-methoxymethoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

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Chemical Property of (5S,8R,9R)-8-benzyl-2-[(1E,3E)-hexa-1,3-dienyl]-8-hydroxy-9-methoxymethoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

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Technology Process of (5S,8R,9R)-8-benzyl-2-[(1E,3E)-hexa-1,3-dienyl]-8-hydroxy-9-methoxymethoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

There total 22 articles about (5S,8R,9R)-8-benzyl-2-[(1E,3E)-hexa-1,3-dienyl]-8-hydroxy-9-methoxymethoxy-3-methyl-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:

: 499120-94-4
(2R,3R,4R)-4-ethyl-2,3-dihydroxy-3-vinyl-4-butanolide

: 660842-28-4
(5S,8R,9R)-8-benzyl-2-[(1E,3E)-hexa-1,3-dienyl]-8-hydroxy-9-methoxymethoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

Guidance literature:: Multi-step reaction with 21 steps

1.1: 79 percent / CSA / acetone / 6 h / 40 °C / 225.02 Torr

2.1: 91 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

3.1: DMAP; pyridine / 4 h / Heating

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

5.1: 6.59 g / CSA / methanol / 48 h / 20 °C

6.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

7.1: 14 percent / tetrahydrofuran / 20 °C

8.1: O₃ / CH₂Cl₂ / 1 h / -78 °C

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

9.1: aq. CF₃CO₂H / 9 h / 20 °C

10.1: 1.11 g / N-iodosuccinimide; n-Bu₄NI / CH₂Cl₂ / 72 h / 20 °C

11.1: 95 percent / pyridine / 12 h / 50 °C

12.1: 94 percent / H₂ / Pd/C / ethanol / 72 h

13.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 9 h / 20 °C

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

14.2: LiBr / tetrahydrofuran; toluene / 1 h / -78 °C

15.1: 146 mg / HF*pyridine; pyridine / 3 h / 20 °C

16.1: Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

16.2: 42 percent / thionyl chloride; pyridine / 0.5 h / 0 °C

17.1: HF*pyridine; pyridine / 6 h / 20 °C

18.1: 30.5 mg / P₂O₅ / CH₂Cl₂ / 2 h / 0 °C

19.1: NH₃ / propan-2-ol / 1 h / 0 °C

20.1: Dess-Martin periodinane / CH₂Cl₂ / 4 h / 0 °C

21.1: 25.8 mg / aq. Na₂CO₃ / 3 h

With pyridine; dmap; N-iodo-succinimide; lithium aluminium tetrahydride; 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; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; acetone; toluene; 6.1: Dess-Martin oxidation / 13.1: Dess-Martin oxidation / 16.1: Dess-Martin oxidation / 20.1: Dess-Martin oxidation;
DOI:10.1246/bcsj.77.1703

Reference yield:

: (2S,3R,4S,5R)-5-Ethyl-4-vinyl-tetrahydro-furan-2,3,4-triol

: 660842-28-4
(5S,8R,9R)-8-benzyl-2-[(1E,3E)-hexa-1,3-dienyl]-8-hydroxy-9-methoxymethoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

Guidance literature:: Multi-step reaction with 22 steps

1.1: 5.60 g / N-iodosuccinimide; n-Bu₄NI / CH₂Cl₂ / 20 h / 20 °C

2.1: 79 percent / CSA / acetone / 6 h / 40 °C / 225.02 Torr

3.1: 91 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

4.1: DMAP; pyridine / 4 h / Heating

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

6.1: 6.59 g / CSA / methanol / 48 h / 20 °C

7.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

8.1: 14 percent / tetrahydrofuran / 20 °C

9.1: O₃ / CH₂Cl₂ / 1 h / -78 °C

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

10.1: aq. CF₃CO₂H / 9 h / 20 °C

11.1: 1.11 g / N-iodosuccinimide; n-Bu₄NI / CH₂Cl₂ / 72 h / 20 °C

12.1: 95 percent / pyridine / 12 h / 50 °C

13.1: 94 percent / H₂ / Pd/C / ethanol / 72 h

14.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 9 h / 20 °C

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

15.2: LiBr / tetrahydrofuran; toluene / 1 h / -78 °C

16.1: 146 mg / HF*pyridine; pyridine / 3 h / 20 °C

17.1: Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

17.2: 42 percent / thionyl chloride; pyridine / 0.5 h / 0 °C

18.1: HF*pyridine; pyridine / 6 h / 20 °C

19.1: 30.5 mg / P₂O₅ / CH₂Cl₂ / 2 h / 0 °C

20.1: NH₃ / propan-2-ol / 1 h / 0 °C

21.1: Dess-Martin periodinane / CH₂Cl₂ / 4 h / 0 °C

22.1: 25.8 mg / aq. Na₂CO₃ / 3 h

With pyridine; dmap; N-iodo-succinimide; lithium aluminium tetrahydride; 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; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; acetone; toluene; 7.1: Dess-Martin oxidation / 14.1: Dess-Martin oxidation / 17.1: Dess-Martin oxidation / 21.1: Dess-Martin oxidation;
DOI:10.1246/bcsj.77.1703

Reference yield:

: 499120-96-6
(2S,3R,4R)-2,3-isopropylidenedioxy-3-vinylhexane-1,4-diol

: 660842-28-4
(5S,8R,9R)-8-benzyl-2-[(1E,3E)-hexa-1,3-dienyl]-8-hydroxy-9-methoxymethoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

Guidance literature:: Multi-step reaction with 19 steps

1.1: DMAP; pyridine / 4 h / Heating

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

3.1: 6.59 g / CSA / methanol / 48 h / 20 °C

4.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

5.1: 14 percent / tetrahydrofuran / 20 °C

6.1: O₃ / CH₂Cl₂ / 1 h / -78 °C

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

7.1: aq. CF₃CO₂H / 9 h / 20 °C

8.1: 1.11 g / N-iodosuccinimide; n-Bu₄NI / CH₂Cl₂ / 72 h / 20 °C

9.1: 95 percent / pyridine / 12 h / 50 °C

10.1: 94 percent / H₂ / Pd/C / ethanol / 72 h

11.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 9 h / 20 °C

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

12.2: LiBr / tetrahydrofuran; toluene / 1 h / -78 °C

13.1: 146 mg / HF*pyridine; pyridine / 3 h / 20 °C

14.1: Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

14.2: 42 percent / thionyl chloride; pyridine / 0.5 h / 0 °C

15.1: HF*pyridine; pyridine / 6 h / 20 °C

16.1: 30.5 mg / P₂O₅ / CH₂Cl₂ / 2 h / 0 °C

17.1: NH₃ / propan-2-ol / 1 h / 0 °C

18.1: Dess-Martin periodinane / CH₂Cl₂ / 4 h / 0 °C

19.1: 25.8 mg / aq. Na₂CO₃ / 3 h

With pyridine; dmap; N-iodo-succinimide; 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; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene; 4.1: Dess-Martin oxidation / 11.1: Dess-Martin oxidation / 14.1: Dess-Martin oxidation / 18.1: Dess-Martin oxidation;
DOI:10.1246/bcsj.77.1703