(5S,10R)-(+)-O-methyl pisiferic acid

Base Information

Chemical Name:(5S,10R)-(+)-O-methyl pisiferic acid
CAS No.:76235-94-4
Molecular Formula:C₂₁H₃₀O₃
Molecular Weight:330.467
Hs Code.:

Synonyms:(5S,10R)-(+)-O-methyl pisiferic acid

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Chemical Property of (5S,10R)-(+)-O-methyl pisiferic acid

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Technology Process of (5S,10R)-(+)-O-methyl pisiferic acid

There total 1 articles about (5S,10R)-(+)-O-methyl pisiferic acid 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:

: 562-13-0
2,2-dimethyl-1,3-cyclohexanedione

: 76235-94-4
(5S,10R)-(+)-O-methyl pisiferic acid

Guidance literature:: Multi-step reaction with 18 steps

1: baker's yeast

3: NaH, KH / dioxane / 1.17 h / Heating

4: 93.2 percent / NaOMe / methanol; benzene / 2 h / Ambient temperature

5: 84.8 percent / pyrrolidine / benzene / 22 h / Heating

6: 51.4 percent / p-TsOH / methanol / 4 h / Ambient temperature

7: 1.) KOH / 1.) MeOH, H₂O, room temp., 5 h; 2.) EtOAc, ether, 0 deg C, 2 min

8: 88.7 percent / DMAP, TfCl / CH₂Cl₂ / 15 min at 0 deg C then 1 h at room temp.

9: PtO₂, H₂ / ethyl acetate / 36 h / Ambient temperature

10: 80 percent / Jones reagent / acetone / 0.17 h / Ambient temperature

11: NaH / benzene / 1 h at 5 deg C and 20 h at room temp.

12: DDQ, AcOH / dioxane / 0.25 h / Ambient temperature

13: NaH / benzene / 0.75 h / Ambient temperature

14: 84.2 percent / p-TsOH / acetic acid / 3.5 h / Heating

15: C₅H₅NHBr₃ / acetic acid / 1 h / Ambient temperature

16: 89.3 percent / 10percent , H₂,Pd-C, conc. H₂SO₄ / ethyl acetate / 13 h / 35 °C

17: 81.9 percent / anh. K₂CO₃ / acetone / 17 h / Heating

18: 110 mg / t-BuOK / dimethylsulfoxide / 1.17 h / 95 °C

With pyrrolidine; dmap; platinum(IV) oxide; potassium hydroxide; palladium on activated charcoal; jones reagent; trifluoromethane sulfonyl chloride; sulfuric acid; potassium tert-butylate; hydrogen; sodium methylate; potassium hydride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; pyridinium hydrobromide perbromide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; methanol; dichloromethane; acetic acid; dimethyl sulfoxide; ethyl acetate; acetone; benzene;
DOI:10.1016/S0040-4020(01)88156-4