Phyllanthocindiol

Base Information

• Chemical Name: Phyllanthocindiol
• CAS No.: 87925-07-3
• Molecular Formula: C₂₅H₃₂O₈
• Molecular Weight: 460.524
• Mol file: 87925-07-3.mol

Synonyms:

Chemical Property of Phyllanthocindiol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Phyllanthocindiol

There total 40 articles about Phyllanthocindiol 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: 96.0%

methyl (2S,3R,3aS,4'S,5'R,6S,7aR)-3-<(tert-butyldimethylsiloxy)methyl>-4'-<(E)-cinnamoyloxy>decahydro-3-hydroxy-5'-methylspiropyran>-6-carboxylate (88671-10-7) → (+)-phyllanthocindiol methyl ester (87925-07-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 23 ℃; for 0.166667h;

DOI:10.1021/jo00179a018

Reference yield: 84.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (+)-Phyllanthocindiol (124516-72-9) → (+)-phyllanthocindiol methyl ester (87925-07-3)

Guidance literature:

In diethyl ether;

DOI:10.1016/S0040-4039(00)99491-7

Reference yield:

Tetrahydro-4H-pyran-4-one (29943-42-8,143562-54-3) → (+)-phyllanthocindiol methyl ester (87925-07-3)

Guidance literature:

Multi-step reaction with 18 steps

1: 100 percent / p-TsOH*H₂O / benzene / 1 h / Heating

2: 91 percent / pyridinium bromide perbromide / tetrahydrofuran / 0.25 h / Ambient temperature

3: 77 percent / t-BuOK / dimethylsulfoxide / 0.25 h / Ambient temperature

4: 1.) t-BuLi, 2.) HMPA / 1.) THF, pentane, 0 deg C, 1 h, 2.) THF, pentane, -78 deg C, 30 min

5: oxalic acid / CH₂Cl₂ / 2 h / Ambient temperature

6: (COCl)2, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

7: ZnBr₂ / CH₂Cl₂ / 23 h / Ambient temperature

8: camphorsulfonic acid (CSA) / benzene / 18 h / Ambient temperature

9: 79 percent / dimethylsulfoxide; tetrahydrofuran / 1.75 h / 0 - 20 °C

11: 229.4 mg / H₂ / 10percent Pd(OH)2/C / ethyl acetate / 0.67 h / Ambient temperature

12: 82 percent / NaIO₄, RuCl₃ / H₂O; CCl₄; acetonitrile / 3 h / Ambient temperature

13: 83 percent / 1,3-dicyclohexylcarbodiimide, 4-pyrrolidinopyridine / CH₂Cl₂ / 1 h / Ambient temperature

14: 80 percent / NaBH₄ / methanol; tetrahydrofuran / 0.67 h / -30 °C

15: 94 percent / 4-pyrrolidinopyridine, Et₃N / pyridine / 48 h / Ambient temperature

16: 77 percent / H₂O, NaHCO₃ / various solvent(s) / 24 h / 130 °C

17: 88 percent / t-Bu₄NF / dimethylsulfoxide / 4 h / 55 °C

18: 83 percent / diethyl ether / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; ruthenium trichloride; sodium tetrahydroborate; sodium periodate; oxalyl dichloride; camphor-10-sulfonic acid; potassium tert-butylate; water; hydrogen; tert.-butyl lithium; pyridinium hydrobromide perbromide; oxalic acid; sodium hydrogencarbonate; 4-pyrrolidin-1-ylpyridine; toluene-4-sulfonic acid; dimethyl sulfoxide; tetra(tert-butyl)-ammonium fluoride; triethylamine; dicyclohexyl-carbodiimide; zinc dibromide; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; tetrachloromethane; diethyl ether; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; acetonitrile; benzene;

upstream raw materials:

diazomethane

(+)-Phyllanthocindiol

methyl (2S,3R,3aS,4'S,5'R,6S,7aR)-3-<(tert-butyldimethylsiloxy)methyl>-4'-<(E)-cinnamoyloxy>decahydro-3-hydroxy-5'-methylspiropyran>-6-carboxylate

(S)-4-(benzyloxy)-2,3-dimethyl-1-butene