(+)-integerrinenic acid lactone

Base Information

• Chemical Name: (+)-integerrinenic acid lactone
• CAS No.: 34081-94-2
• Molecular Formula: C₁₀H₁₄O₄
• Molecular Weight: 198.219
• Mol file: 34081-94-2.mol

Synonyms:(+)-integerrinenic acid lactone

Chemical Property of (+)-integerrinenic acid lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-integerrinenic acid lactone

There total 1 articles about (+)-integerrinenic acid lactone 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:

trans-6-Cyan-6-hydroxy-5-methyl-2-hepten-3-carbonsaeure (77147-54-7) → Integerrinecic acid (469-45-4,6582-63-4,6703-97-5,6883-40-5,10407-68-8,10407-69-9,10407-70-2,10407-71-3,10407-73-5,13588-16-4,86747-28-6,86747-29-7) + 5-Eth-(E)-ylidene-2,3-dimethyl-6-oxo-tetrahydro-pyran-2-carboxylic acid (3055-21-8,10407-74-6,10407-75-7,10407-76-8,28822-16-4,34081-94-2,86747-27-5)

Guidance literature:

With hydrogenchloride; 1.) 12 h, 2.) 6 h;

DOI:10.1002/ardp.19803131006

Reference yield:

(+)-integerrinenic acid lactone (34081-94-2) → (-)-integerrimine (130-01-8,480-79-5,480-80-8,82535-12-4,86782-21-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / 2-chloro-1-methylpyridinium iodide, Et₃N / CH₂Cl₂ / Ambient temperature

2: 57 percent / 30 percent H₂O₂, aq. LiOH / tetrahydrofuran / a) 0 deg C, 1 h, b) r.t., 3 h

3: 87 percent / a) 2,6-lutidine, b) AcOH / a) CH₂Cl₂, 1 h, b) THF, H₂O, r.t., 8 h

4: 1) Et₃N, (EtO)2POCl, 2) 4-(dimethylamino)pyridine, n-BuLi / 1) THF, r.t., 3 h, 2) THF, hexane, r.t., 5 h

5: 67 percent / NH₄F / methanol; H₂O / 4 h / 60 - 65 °C

6: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

7: n-Bu₄NF / CH₂Cl₂; acetonitrile / 0.5 h

8: 67 percent / 48 percent aq. HF / acetonitrile / 12 h / Ambient temperature

With 2,6-dimethylpyridine; dmap; ammonium fluoride; lithium hydroxide; n-butyllithium; hydrogen fluoride; tetrabutyl ammonium fluoride; 2-chloro-1-methyl-pyridinium iodide; dihydrogen peroxide; diethyl chlorophosphate; acetic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;

DOI:10.1021/jo00034a017

Reference yield:

(+/-)-integerrinecic acid lactone (3055-21-8,10407-74-6,10407-75-7,10407-76-8,28822-16-4,34081-94-2,86747-27-5) → (+/-)-integerrimine (130-01-8,480-79-5,480-80-8,82535-12-4,86782-21-0)

Guidance literature:

Multi-step reaction with 15 steps

1: 98 percent / 2-chloro-1-methylpyridinium iodide, Et₃N / CH₂Cl₂

2: 71 percent / LiOH*H₂O, 28percent H₂O₂ / H₂O; tetrahydrofuran / 3 h

3: 92 percent / NaI, diisopropylethylamine / 1,2-dimethoxy-ethane / RT, overnight, reflux, 1 h

4: 88 percent / NaI, diisopropylethylamine / 1,2-dimethoxy-ethane / 12 h / Heating

5: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3.5 h / Ambient temperature

6: 89 percent / 28percent H₂O₂, 0.1 M ammonium molybdate / acetone; H₂O / 3 h / Ambient temperature

7: 86 percent / NaI, diisopropylethylamine / 1,2-dimethoxy-ethane / 6 h / Ambient temperature

8: 4.10 g / 1 N NaOH / 1,2-dimethoxy-ethane; H₂O / 5 h / Ambient temperature

9: 91 percent / 2-chloro-1-methylpyridinium iodide, Et₃N / CH₂Cl₂ / 24 h / Ambient temperature

10: 81 percent / DMAP, n-BuLi / hexane / 4.5 h / Ambient temperature

11: 82 percent / NH₄F / methanol; H₂O / 6 h / 60 °C

12: 73 percent / 28percent H₂O₂, 0.1 M ammonium molybdate / ethanol; H₂O / 1.5 h

13: 41 percent / (triphenylmethyl)lithium / tetrahydrofuran / 2 h / -78 - -60 °C

14: 27 percent / 1 N H₂SO₄, Zn / 1,2-dimethoxy-ethane / 1 h / Ambient temperature

15: 86 percent / 1 N H₂SO₄ / 1,2-dimethoxy-ethane / 2.5 h / 40 °C

With dmap; ammonium fluoride; lithium hydroxide; sodium hydroxide; n-butyllithium; ammonium molybdate; sulfuric acid; tetrabutyl ammonium fluoride; 2-chloro-1-methyl-pyridinium iodide; trityllithium; dihydrogen peroxide; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; zinc; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; acetone;

DOI:10.1021/ja00322a036

upstream raw materials:

trans-6-Cyan-6-hydroxy-5-methyl-2-hepten-3-carbonsaeure

Downstream raw materials:

Dihydrosyneilesinolid B

(-)-integerrimine

(+/-)-integerrinecic acid

(+/-)-integerrimine