(+/-)-methyl trans-5,6-epoxy-7-hydroxyheptanoate

Base Information

• Chemical Name: (+/-)-methyl trans-5,6-epoxy-7-hydroxyheptanoate
• CAS No.: 77519-23-4
• Molecular Formula: C₈H₁₄O₄
• Molecular Weight: 174.197
• Mol file: 77519-23-4.mol

Synonyms:

Chemical Property of (+/-)-methyl trans-5,6-epoxy-7-hydroxyheptanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-methyl trans-5,6-epoxy-7-hydroxyheptanoate

There total 15 articles about (+/-)-methyl trans-5,6-epoxy-7-hydroxyheptanoate 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: 98.0%

C29H30O9S (73957-98-9) → (+/-)-methyl trans-5,6-epoxy-7-hydroxyheptanoate (73957-99-0,77341-36-7,77519-23-4,79356-62-0,79356-66-4,114530-61-9,127760-14-9)

Guidance literature:

With potassium carbonate; In methanol; at 23 ℃; for 2h;

DOI:10.1021/ja00524a045

Reference yield: 77.0%

cis-7-hydroxy-5-heptenoic acid,methyl ester (76871-77-7) → (+/-)-methyl trans-5,6-epoxy-7-hydroxyheptanoate (73957-99-0,77341-36-7,77519-23-4,79356-62-0,79356-66-4,114530-61-9,127760-14-9)

Guidance literature:

With 3-chlorobenzoate; In dichloromethane; at 23 ℃; for 14h;

DOI:10.1016/S0040-4039(00)92873-9

Reference yield:

C26H22O8 (55797-81-4,105453-39-2) → (+/-)-methyl trans-5,6-epoxy-7-hydroxyheptanoate (73957-99-0,77341-36-7,77519-23-4,79356-62-0,79356-66-4,114530-61-9,127760-14-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 96 percent / benzoic acid / 1,2-dimethoxy-ethane / 4 h / Heating

2: 100 percent / H₂SO₄ / 3 h / 23 °C

3: 93 percent / 95percent zinc amalgam, dry hydrogen chloride / diethyl ether / 6 h / 15 °C

4: 100 percent / H₂ / 10percent Pd/C / methanol / 23 °C

5: 99 percent / dry hydroden chloride / 72 h / 23 °C

6: 98 percent / pyridine / 1.) 23 deg C, 6 h, 2.) 50 deg C, 3h

7: 98 percent / K₂CO₃ / methanol / 2 h / 23 °C

With pyridine; hydrogenchloride; amalgamated zinc; sulfuric acid; hydrogen; potassium carbonate; benzoic acid; palladium on activated charcoal; In methanol; 1,2-dimethoxyethane; diethyl ether;

DOI:10.1021/ja00524a045

upstream raw materials:

methyl (Z)-7-hydroxy-5-heptenoate

cis-7-hydroxy-5-heptenoic acid,methyl ester

C₂₉H₃₀O₉S

2-(6-hydroxy-4-hexynyl)-1,3-dioxolane

Downstream raw materials:

methyl 10-formyl-5,6E-epoxy-7E,9E-decadienoate

(7E,9E,11Z,14Z)-(5S,6R)-6-[2-(4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester

4-[(2S,3S)-3-((1Z,3E)-5-Oxo-penta-1,3-dienyl)-oxiranyl]-butyric acid methyl ester

(7E,9E,11Z,14Z)-6-[2-Amino-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester

Refernces

• 1、 Egger, Julian,Bretscher, Peter,Freigang, Stefan,Kopf, Manfred,Carreira, Erick M.. "Synthesis of epoxyisoprostanes: Effects in reducing secretion of pro-inflammatory cytokines IL-6 and IL-12". . p. 5382 - 5385. Retrieved 2013/06/26.
• 2、 Tolstikov, G. A.,Miftakhov, M. S.,Tolstikov, A. G.. "PROSTANOIDS. X. SYNTHESIS OF THE METHYL ESTER OF (+/-)-11,12,14,15-BISDEHYDROLEUCOTRIENE A4 AND ITS ANALOGS". . p. 2076 - 2081. Retrieved 2007/10/02.