(2R,6S,7R,8R)-7-((E)-But-1-en-3-ynyl)-2-((E)-pent-2-en-4-ynyl)-1-aza-spiro[5.5]undecan-8-ol

Base Information

• Chemical Name: (2R,6S,7R,8R)-7-((E)-But-1-en-3-ynyl)-2-((E)-pent-2-en-4-ynyl)-1-aza-spiro[5.5]undecan-8-ol
• CAS No.: 85718-94-1
• Molecular Formula: C₁₉H₂₅NO
• Molecular Weight: 283.414
• Mol file: 85718-94-1.mol

Synonyms:

Chemical Property of (2R,6S,7R,8R)-7-((E)-But-1-en-3-ynyl)-2-((E)-pent-2-en-4-ynyl)-1-aza-spiro[5.5]undecan-8-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,6S,7R,8R)-7-((E)-But-1-en-3-ynyl)-2-((E)-pent-2-en-4-ynyl)-1-aza-spiro[5.5]undecan-8-ol

There total 34 articles about (2R,6S,7R,8R)-7-((E)-But-1-en-3-ynyl)-2-((E)-pent-2-en-4-ynyl)-1-aza-spiro[5.5]undecan-8-ol 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:

C13H19NO2 (104270-41-9) → d,l-histrionicotoxin (34272-51-0,85718-94-1,91879-07-1,34685-67-1)

Guidance literature:

Multi-step reaction with 16 steps

2: P₂S₅ / pyridine / 80 °C

3: NaHCO₃ / CH₂Cl₂ / Ambient temperature

4: NaOH / methanol; H₂O / -20 °C

5: PCC / CH₂Cl₂ / Ambient temperature

6: nBuLi / tetrahydrofuran / -78 °C

7: NaOEt / ethanol / 50 °C

8: CH₃Li / tetrahydrofuran

9: 38 percent / NaBH₃CN / cyclohexane / Ambient temperature

11: nBu₄NF / tetrahydrofuran

12: 1.)Et₃N, 2.) HCl / 1.) methylene dichloride, 2.) Et₂O, CH₂Cl₂

13: 1.) LiBr / 1.) DMF, 50 deg C, 2.) CH₃CN, 160 deg C

14: 1.) LDA / 1.) THF, room temp.

15: nBu₄NF / tetrahydrofuran

16: NaOH / methanol

With hydrogenchloride; sodium hydroxide; n-butyllithium; tetraphosphorus decasulfide; tetrabutyl ammonium fluoride; methyllithium; sodium ethanolate; sodium cyanoborohydride; sodium hydrogencarbonate; triethylamine; pyridinium chlorochromate; lithium bromide; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; cyclohexane; water;

DOI:10.1016/S0040-4039(00)98253-4

Reference yield:

C13H19NO2 (104270-41-9) → (2R,6S,7R,8R)-7-((E)-But-1-en-3-ynyl)-2-((E)-pent-2-en-4-ynyl)-1-aza-spiro[5.5]undecan-8-ol (34272-51-0,85718-94-1,91879-07-1,34685-67-1)

Guidance literature:

Multi-step reaction with 16 steps

2: P₂S₅ / pyridine / 80 °C

3: NaHCO₃ / CH₂Cl₂ / Ambient temperature

4: NaOH / methanol; H₂O / -20 °C

5: PCC / CH₂Cl₂ / Ambient temperature

6: nBuLi / tetrahydrofuran / -78 °C

7: NaOEt / ethanol / 50 °C

8: CH₃Li / tetrahydrofuran

9: 38 percent / NaBH₃CN / cyclohexane / Ambient temperature

11: nBu₄NF / tetrahydrofuran

12: 1.)Et₃N, 2.) HCl / 1.) methylene dichloride, 2.) Et₂O, CH₂Cl₂

13: 1.) LiBr / 1.) DMF, 50 deg C, 2.) CH₃CN, 160 deg C

14: 1.) LDA / 1.) THF, room temp.

15: nBu₄NF / tetrahydrofuran

16: NaOH / methanol

With hydrogenchloride; sodium hydroxide; n-butyllithium; tetraphosphorus decasulfide; tetrabutyl ammonium fluoride; methyllithium; sodium ethanolate; sodium cyanoborohydride; sodium hydrogencarbonate; triethylamine; pyridinium chlorochromate; lithium bromide; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; cyclohexane; water;

DOI:10.1016/S0040-4039(00)98253-4

Reference yield:

Acetic acid (6R,7R,8R)-7-but-3-enyl-2-oxo-1-aza-spiro[5.5]undec-8-yl ester (56459-26-8) → d,l-histrionicotoxin (34272-51-0,85718-94-1,91879-07-1,34685-67-1)

Guidance literature:

Multi-step reaction with 17 steps

3: P₂S₅ / pyridine / 80 °C

4: NaHCO₃ / CH₂Cl₂ / Ambient temperature

5: NaOH / methanol; H₂O / -20 °C

6: PCC / CH₂Cl₂ / Ambient temperature

7: nBuLi / tetrahydrofuran / -78 °C

8: NaOEt / ethanol / 50 °C

9: CH₃Li / tetrahydrofuran

10: 38 percent / NaBH₃CN / cyclohexane / Ambient temperature

12: nBu₄NF / tetrahydrofuran

13: 1.)Et₃N, 2.) HCl / 1.) methylene dichloride, 2.) Et₂O, CH₂Cl₂

14: 1.) LiBr / 1.) DMF, 50 deg C, 2.) CH₃CN, 160 deg C

15: 1.) LDA / 1.) THF, room temp.

16: nBu₄NF / tetrahydrofuran

17: NaOH / methanol

With hydrogenchloride; sodium hydroxide; n-butyllithium; tetraphosphorus decasulfide; tetrabutyl ammonium fluoride; methyllithium; sodium ethanolate; sodium cyanoborohydride; sodium hydrogencarbonate; triethylamine; pyridinium chlorochromate; lithium bromide; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; cyclohexane; water;

DOI:10.1016/S0040-4039(00)98253-4

upstream raw materials:

Acetic acid (6S,7R,8R)-7-((E)-but-1-en-3-ynyl)-2-((Z)-pent-2-en-4-ynyl)-1-aza-spiro[5.5]undec-8-yl ester

C₁₃H₁₉NO₂

Acetic acid (6R,7R,8R)-7-but-3-enyl-2-oxo-1-aza-spiro[5.5]undec-8-yl ester

Acetic acid (6R,7R,8R)-7-((Z)-3-acetoxy-propenyl)-2-oxo-1-aza-spiro[5.5]undec-8-yl ester