4,5-Secoakuammilan-17-oic acid, 2,5-epoxy-1,2-dihydro-16-(hydroxymethy l)-, methyl ester, (2alpha,16S)-

Base Information

Chemical Name:4,5-Secoakuammilan-17-oic acid, 2,5-epoxy-1,2-dihydro-16-(hydroxymethy l)-, methyl ester, (2alpha,16S)-
CAS No.:26988-11-4
Molecular Formula:C₂₁H₂₆N₂O₄
Molecular Weight:370.448
Hs Code.:
Mol file:26988-11-4.mol

Synonyms:4,5-Secoakuammilan-17-oicacid, 2,5-epoxy-1,2-dihydro-16-(hydroxymethyl)-, methyl ester, (2a,16S)-; Lonicerine (8CI);11a,6a-(Epoxyethano)-1,5-methano-11H-azocino[3,4-b]indole-6-carboxylic acid,4-ethylidene-1,2,3,4,5,6-hexahydro-6-(hydroxymethyl)-, methyl ester, [1S-(1a,4E,5a,6a,6ab,11ab)]-; 16-Epiaspidodasycarpine; Lonicerine (alkaloid)

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Chemical Property of 4,5-Secoakuammilan-17-oic acid, 2,5-epoxy-1,2-dihydro-16-(hydroxymethy l)-, methyl ester, (2alpha,16S)-

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Technology Process of 4,5-Secoakuammilan-17-oic acid, 2,5-epoxy-1,2-dihydro-16-(hydroxymethy l)-, methyl ester, (2alpha,16S)-

There total 17 articles about 4,5-Secoakuammilan-17-oic acid, 2,5-epoxy-1,2-dihydro-16-(hydroxymethy l)-, methyl ester, (2alpha,16S)- 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: 76.0%

: C₂₈H₃₂N₂O₆S

: 2744-47-0,26988-11-4
aspidodasycarpine

Guidance literature:: With naphthalene radical anion sodium salt; In tetrahydrofuran; at -78 ℃; for 0.0833333h; Inert atmosphere;
DOI:10.1021/jacs.6b00764

Reference yield:

: C₂₉H₂₅N₃O₇S₂

: 2744-47-0,26988-11-4
aspidodasycarpine

Guidance literature:: Multi-step reaction with 14 steps

1.1: sodium tetrahydroborate / methanol; dichloromethane / 0.5 h / 0 °C / Inert atmosphere

2.1: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / 22 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / cyclohexane; dichloromethane / 2 h / -78 °C / Inert atmosphere

4.1: sodium carbonate / methanol; dichloromethane; water / 3 h / 22 °C / Inert atmosphere

5.1: trifluorormethanesulfonic acid / 1,4-dioxane / 2 h / 22 °C / Inert atmosphere; Molecular sieve

6.1: sodium tetrahydroborate / methanol; dichloromethane / 0.17 h / 22 °C / Inert atmosphere

6.2: 2 h / 0 °C / Inert atmosphere

7.1: sodium hydrogencarbonate; N-iodo-succinimide / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

8.1: lithium tert-butoxide / dimethyl sulfoxide / 1 h / 120 °C / Microwave irradiation; Inert atmosphere

9.1: (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; hydrogen / tetrahydrofuran / 5 h / 22 °C / Inert atmosphere

9.2: 48 h / 22 °C / Inert atmosphere

10.1: sodium tetrahydroborate / methanol / 2 h / 0 °C / Inert atmosphere

11.1: 2-azatricyclo[3.3.1.1^3,7]dec-2-yloxidanyl; sodium chlorite; 2-methyl-but-2-ene / dichloromethane / 10 h / 22 °C / pH 4 / Inert atmosphere

12.1: methanol; hexane / 0.17 h / 0 °C / Inert atmosphere

13.1: boron tribromide / dichloromethane / 1 h / -78 °C / Inert atmosphere

14.1: naphthalene radical anion sodium salt / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere

With sodium chlorite; sodium tetrahydroborate; N-iodo-succinimide; 2-methyl-but-2-ene; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; 2-azatricyclo[3.3.1.1^3,7]dec-2-yloxidanyl; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; hydrogen; naphthalene radical anion sodium salt; boron tribromide; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium carbonate; lithium tert-butoxide; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; cyclohexane; water; dimethyl sulfoxide; 4.1: |Aldol Condensation;
DOI:10.1021/jacs.6b00764

Reference yield:

: C₂₉H₂₇N₃O₇S₂

: 2744-47-0,26988-11-4
aspidodasycarpine

Guidance literature:: Multi-step reaction with 13 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / 22 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / cyclohexane; dichloromethane / 2 h / -78 °C / Inert atmosphere

3.1: sodium carbonate / methanol; dichloromethane; water / 3 h / 22 °C / Inert atmosphere

4.1: trifluorormethanesulfonic acid / 1,4-dioxane / 2 h / 22 °C / Inert atmosphere; Molecular sieve

5.1: sodium tetrahydroborate / methanol; dichloromethane / 0.17 h / 22 °C / Inert atmosphere

5.2: 2 h / 0 °C / Inert atmosphere

6.1: sodium hydrogencarbonate; N-iodo-succinimide / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

7.1: lithium tert-butoxide / dimethyl sulfoxide / 1 h / 120 °C / Microwave irradiation; Inert atmosphere

8.1: (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; hydrogen / tetrahydrofuran / 5 h / 22 °C / Inert atmosphere

8.2: 48 h / 22 °C / Inert atmosphere

9.1: sodium tetrahydroborate / methanol / 2 h / 0 °C / Inert atmosphere

10.1: 2-azatricyclo[3.3.1.1^3,7]dec-2-yloxidanyl; sodium chlorite; 2-methyl-but-2-ene / dichloromethane / 10 h / 22 °C / pH 4 / Inert atmosphere

11.1: methanol; hexane / 0.17 h / 0 °C / Inert atmosphere

12.1: boron tribromide / dichloromethane / 1 h / -78 °C / Inert atmosphere

13.1: naphthalene radical anion sodium salt / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere

With sodium chlorite; sodium tetrahydroborate; N-iodo-succinimide; 2-methyl-but-2-ene; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; 2-azatricyclo[3.3.1.1^3,7]dec-2-yloxidanyl; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; hydrogen; naphthalene radical anion sodium salt; boron tribromide; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium carbonate; lithium tert-butoxide; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; cyclohexane; water; dimethyl sulfoxide; 3.1: |Aldol Condensation;
DOI:10.1021/jacs.6b00764