catalpol, β-ethyl acetal

Base Information

Chemical Name:catalpol, β-ethyl acetal
CAS No.:121681-28-5
Molecular Formula:C₁₁H₁₆O₅
Molecular Weight:228.245
Hs Code.:

Synonyms:

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Chemical Property of catalpol, β-ethyl acetal

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Technology Process of catalpol, β-ethyl acetal

There total 16 articles about catalpol, β-ethyl acetal 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:

: 34212-44-7,34213-73-5
Ethyl-2,3-dideoxy-4-O-acetyl-D-glycero-pent-2-enopyranosid

: 121681-28-5
catalpol, β-ethyl acetal

Guidance literature:: Multi-step reaction with 16 steps

1: 1.) n-BuLi(hexane), diisopropylamine / 1.) THF, 0 deg C, 15 min, then -78 deg C, THF, 3 min, 2.) THF, HMPA, to 0 deg C, 35 min

2: toluene / 20 h / 80 °C

3: KF, KHCO₃, water / hexamethylphosphoric acid triamide / 8 h / 25 °C

4: hexamethylphosphoric acid triamide / 12 h

5: 1.) LDA / 1.) THF, -78 deg C, 1 h, 2.) THF, -25 deg C to 25 deg C, 1.5 h

6: 1.) LDA / 1.) THF; -78 deg C, 30 min, 2.) benzene, -78 deg C, 1 h, then to 25 deg C, 30 min

7: 100 percent / Et₃N, MeNCO / benzene / 14 h, 25 deg C, then 85 deg C, 1 h

8: 1.) saturated NaHCO₃, mCPBA / 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) benzene, reflux, 5 h

9: 1.) n-BuLi, DIBAL / 1.) -78 deg C, 2.) THF -78 deg C, 1 h, then warming to 0 deg C, 5 min

10: 52 percent / imidazole / dimethylformamide / 16 h / 45 °C

11: 321 mg / 3,5-dinitroperoxybenzoic acid(3,5-DNBA), NaH₂PO₄ / 4,4'-thiobis(Z-t-butyl-6-methylphenol) / CH₂Cl₂ / 5 h / 25 °C

12: 74 percent / boric acid, H₂ / Rh/Al / methanol; H₂O / 1.5 h / 25 °C

13: 35 mg / MsCl, Et₃N / CH₂Cl₂ / 0.5 h / 25 °C

14: NaBH₄, CeCl₃ / methanol / investigation ofreduction with var. reagents

15: 90 percent / dihydridotris(triphenylphosphine)ruthenium(II) / ethanol / 5 h / Heating

16: 2.5 mg / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 25 °C

With 1H-imidazole; potassium fluoride; sodium tetrahydroborate; sodium dihydrogenphosphate; n-butyllithium; cerium(III) chloride; dihydridotris(triphenylphosphine)ruthenium(II); 3,5-dinitrobenzoperoxoic acid; tetrabutyl ammonium fluoride; water; hydrogen; boric acid; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium hydrogencarbonate; methanesulfonyl chloride; triethylamine; diisopropylamine; methyl isocyanate; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; rhodium on aluminium; 6,6'-di-tert-butyl-4,4'-thiodi-o-cresol; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1016/S0040-4020(01)85940-8

Reference yield:

: 98454-78-5
(2R-trans)-2-ethoxy-3,6-dihydro-2H-pyran-3-acetic acid, methyl ester

: 121681-28-5
catalpol, β-ethyl acetal

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) LDA / 1.) THF, -78 deg C, 1 h, 2.) THF, -25 deg C to 25 deg C, 1.5 h

2: 1.) LDA / 1.) THF; -78 deg C, 30 min, 2.) benzene, -78 deg C, 1 h, then to 25 deg C, 30 min

3: 100 percent / Et₃N, MeNCO / benzene / 14 h, 25 deg C, then 85 deg C, 1 h

4: 1.) saturated NaHCO₃, mCPBA / 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) benzene, reflux, 5 h

5: 1.) n-BuLi, DIBAL / 1.) -78 deg C, 2.) THF -78 deg C, 1 h, then warming to 0 deg C, 5 min

6: 52 percent / imidazole / dimethylformamide / 16 h / 45 °C

7: 321 mg / 3,5-dinitroperoxybenzoic acid(3,5-DNBA), NaH₂PO₄ / 4,4'-thiobis(Z-t-butyl-6-methylphenol) / CH₂Cl₂ / 5 h / 25 °C

8: 74 percent / boric acid, H₂ / Rh/Al / methanol; H₂O / 1.5 h / 25 °C

9: 35 mg / MsCl, Et₃N / CH₂Cl₂ / 0.5 h / 25 °C

10: NaBH₄, CeCl₃ / methanol / investigation ofreduction with var. reagents

11: 90 percent / dihydridotris(triphenylphosphine)ruthenium(II) / ethanol / 5 h / Heating

12: 2.5 mg / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 25 °C

With 1H-imidazole; sodium tetrahydroborate; sodium dihydrogenphosphate; n-butyllithium; cerium(III) chloride; dihydridotris(triphenylphosphine)ruthenium(II); 3,5-dinitrobenzoperoxoic acid; tetrabutyl ammonium fluoride; hydrogen; boric acid; diisobutylaluminium hydride; sodium hydrogencarbonate; methanesulfonyl chloride; triethylamine; methyl isocyanate; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; rhodium on aluminium; 6,6'-di-tert-butyl-4,4'-thiodi-o-cresol; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4020(01)85940-8

Reference yield:

: 121681-21-8
tert-Butyl-[1-((3S,6R)-6-ethoxy-3,6-dihydro-2H-pyran-3-yloxy)-vinyloxy]-dimethyl-silane

: 121681-28-5
catalpol, β-ethyl acetal

Guidance literature:: Multi-step reaction with 15 steps

1: toluene / 20 h / 80 °C

2: KF, KHCO₃, water / hexamethylphosphoric acid triamide / 8 h / 25 °C

3: hexamethylphosphoric acid triamide / 12 h

4: 1.) LDA / 1.) THF, -78 deg C, 1 h, 2.) THF, -25 deg C to 25 deg C, 1.5 h

5: 1.) LDA / 1.) THF; -78 deg C, 30 min, 2.) benzene, -78 deg C, 1 h, then to 25 deg C, 30 min

6: 100 percent / Et₃N, MeNCO / benzene / 14 h, 25 deg C, then 85 deg C, 1 h

7: 1.) saturated NaHCO₃, mCPBA / 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) benzene, reflux, 5 h

8: 1.) n-BuLi, DIBAL / 1.) -78 deg C, 2.) THF -78 deg C, 1 h, then warming to 0 deg C, 5 min

9: 52 percent / imidazole / dimethylformamide / 16 h / 45 °C

10: 321 mg / 3,5-dinitroperoxybenzoic acid(3,5-DNBA), NaH₂PO₄ / 4,4'-thiobis(Z-t-butyl-6-methylphenol) / CH₂Cl₂ / 5 h / 25 °C

11: 74 percent / boric acid, H₂ / Rh/Al / methanol; H₂O / 1.5 h / 25 °C

12: 35 mg / MsCl, Et₃N / CH₂Cl₂ / 0.5 h / 25 °C

13: NaBH₄, CeCl₃ / methanol / investigation ofreduction with var. reagents

14: 90 percent / dihydridotris(triphenylphosphine)ruthenium(II) / ethanol / 5 h / Heating

15: 2.5 mg / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 25 °C

With 1H-imidazole; potassium fluoride; sodium tetrahydroborate; sodium dihydrogenphosphate; n-butyllithium; cerium(III) chloride; dihydridotris(triphenylphosphine)ruthenium(II); 3,5-dinitrobenzoperoxoic acid; tetrabutyl ammonium fluoride; water; hydrogen; boric acid; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium hydrogencarbonate; methanesulfonyl chloride; triethylamine; methyl isocyanate; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; rhodium on aluminium; 6,6'-di-tert-butyl-4,4'-thiodi-o-cresol; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1016/S0040-4020(01)85940-8