1β,3α-specionin

Base Information

• Chemical Name: 1β,3α-specionin
• CAS No.: 113532-00-6
• Molecular Formula: C₂₀H₂₆O₈
• Molecular Weight: 394.422
• Mol file: 113532-00-6.mol

Synonyms:1β,3α-specionin

Chemical Property of 1β,3α-specionin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1β,3α-specionin

There total 155 articles about 1β,3α-specionin 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: 86.0%

4-Benzyloxy-benzoic acid (1aS,1bS,2R,4R,5aR,6S,6aS)-2,4-diethoxy-1a-hydroxymethyl-octahydro-1,3-dioxa-cyclopropa[a]inden-6-yl ester (121784-83-6) → 1β,3α-specionin (113532-00-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 45h;

DOI:10.1016/S0040-4020(01)85940-8

Reference yield:

p-(benzyloxy)benzoic acid (1486-51-7) → 1β,3α-specionin (113532-00-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / oxalyl chloride, DMF / CH₂Cl₂ / 2 h

2: Et₃N / CH₂Cl₂ / 24 h

3: 78 percent / H₂ / 10percent Pd/C / ethanol / 3 h

With oxalyl dichloride; hydrogen; triethylamine; N,N-dimethyl-formamide; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1139/v94-271

Reference yield:

Ethyl-2,3-dideoxy-4-O-acetyl-D-glycero-pent-2-enopyranosid (34212-44-7,34213-73-5) → 1β,3α-specionin (113532-00-6)

Guidance literature:

Multi-step reaction with 19 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: 3.4 mg / DCC / DMAP / CH₂Cl₂ / 72 h

17: 1.) Hg(II)(OAc)2, 2.) Bu₃SnH / 1.) EtOH, 1 h, 25 deg C, 2.) benzene, 0 deg C, 30 min

18: 45 percent / n-butylammonium fluoride / tetrahydrofuran / 30 h / 25 °C

19: 86 percent / H₂ / 10 percent Pd(C) / ethanol / 45 h

With 1H-imidazole; tetranormalbutyl ammonium fluoride; potassium fluoride; sodium tetrahydroborate; sodium dihydrogenphosphate; n-butyllithium; cerium(III) chloride; dihydridotris(triphenylphosphine)ruthenium(II); 3,5-dinitrobenzoperoxoic acid; mercury(II) diacetate; water; hydrogen; tri-n-butyl-tin hydride; boric acid; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium hydrogencarbonate; methanesulfonyl chloride; triethylamine; diisopropylamine; methyl isocyanate; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; lithium diisopropyl amide; dmap; palladium on activated charcoal; 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

upstream raw materials:

4-Hydroxy-benzoic acid (1aS,1bS,2R,4R,5aR,6S,6aS)-1a-acetoxymethyl-2,4-diethoxy-octahydro-1,3-dioxa-cyclopropa[a]inden-6-yl ester

1β,3β-specionin

4-Benzyloxy-benzoic acid (1aS,1bS,2R,4R,5aR,6S,6aS)-2,4-diethoxy-1a-hydroxymethyl-octahydro-1,3-dioxa-cyclopropa[a]inden-6-yl ester

p-benzyloxybenzaldehyde

Downstream raw materials:

(-)-specionin