2-Heptenoic acid, 2,4-diethyl-7-(methoxymethoxy)-6-methyl-5-(phenylmethoxy)-, ethyl ester, (2E,4R,5R,6R)-

Base Information

• Chemical Name: 2-Heptenoic acid, 2,4-diethyl-7-(methoxymethoxy)-6-methyl-5-(phenylmethoxy)-, ethyl ester, (2E,4R,5R,6R)-
• CAS No.: 872615-33-3
• Molecular Formula: C23H36O5
• Molecular Weight: 392.536
• Mol file: 872615-33-3.mol

Synonyms:

Chemical Property of 2-Heptenoic acid, 2,4-diethyl-7-(methoxymethoxy)-6-methyl-5-(phenylmethoxy)-, ethyl ester, (2E,4R,5R,6R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Heptenoic acid, 2,4-diethyl-7-(methoxymethoxy)-6-methyl-5-(phenylmethoxy)-, ethyl ester, (2E,4R,5R,6R)-

There total 9 articles about 2-Heptenoic acid, 2,4-diethyl-7-(methoxymethoxy)-6-methyl-5-(phenylmethoxy)-, ethyl ester, (2E,4R,5R,6R)- 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: 84.0%

(E)-(4R,5R,6R)-2,4-Diethyl-5-hydroxy-7-methoxymethoxy-6-methyl-hept-2-enoic acid ethyl ester (872615-32-2) + benzyl bromide (100-39-0) → (E)-(4R,5R,6R)-5-Benzyloxy-2,4-diethyl-7-methoxymethoxy-6-methyl-hept-2-enoic acid ethyl ester (872615-33-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran;

DOI:10.1021/ol0521329

Reference yield:

(E)-(S)-5-Methoxymethoxy-4-methyl-pent-2-en-1-ol (872615-26-4) → (E)-(4R,5R,6R)-5-Benzyloxy-2,4-diethyl-7-methoxymethoxy-6-methyl-hept-2-enoic acid ethyl ester (872615-33-3)

Guidance literature:

Multi-step reaction with 5 steps

1: TBHP; Ti(O-iPr)4; D-tartaric acid diethyl ester / -23 °C

2: 62 percent / CuI / diethyl ether / -50 - -40 °C

3: 52 percent / RuCl₂(PPh₃)3 / benzene

4: 76 percent / benzene / Heating

5: 84 percent / NaH / tetrahydrofuran

With titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; tris(triphenylphosphine)ruthenium(II) chloride; diethyl (2S,3S)-tartrate; sodium hydride; In tetrahydrofuran; diethyl ether; benzene; 4: Horner-Wittig reaction;

DOI:10.1021/ol0521329

Reference yield:

Acetic acid (R)-3-methoxymethoxy-2-methyl-propyl ester (872615-42-4) → (E)-(4R,5R,6R)-5-Benzyloxy-2,4-diethyl-7-methoxymethoxy-6-methyl-hept-2-enoic acid ethyl ester (872615-33-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 87 percent / K₂CO₃ / methanol

2: (COCl)2; DMSO; triethylamine / CH₂Cl₂

3: 90 percent / DIBAL-H / CH₂Cl₂ / -78 °C

4: TBHP; Ti(O-iPr)4; D-tartaric acid diethyl ester / -23 °C

5: 62 percent / CuI / diethyl ether / -50 - -40 °C

6: 52 percent / RuCl₂(PPh₃)3 / benzene

7: 76 percent / benzene / Heating

8: 84 percent / NaH / tetrahydrofuran

With titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; tris(triphenylphosphine)ruthenium(II) chloride; oxalyl dichloride; diethyl (2S,3S)-tartrate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene; 2: Swern oxidation / 3: Horner-Wittig reaction / 8: Horner-Wittig reaction;

DOI:10.1021/ol0521329

upstream raw materials:

(E)-(4R,5R,6R)-2,4-Diethyl-5-hydroxy-7-methoxymethoxy-6-methyl-hept-2-enoic acid ethyl ester

benzyl bromide

Acetic acid (R)-3-methoxymethoxy-2-methyl-propyl ester

(E)-(S)-5-Methoxymethoxy-4-methyl-pent-2-en-1-ol

Downstream raw materials:

(E)-(4R,5R,6R)-5-Benzyloxy-2,4-diethyl-7-methoxymethoxy-6-methyl-hept-2-en-1-ol

(2E,4E,9E)-(6R,7S,8R)-7-Benzyloxy-10-(tert-butyl-diphenyl-silanyloxymethyl)-8-ethyl-6-methyl-dodeca-2,4,9-trienoic acid methyl ester

(2E,7E)-(4R,5S,6R)-5-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxymethyl)-6-ethyl-4-methyl-deca-2,7-dienoic acid methyl ester

(2E,7E)-(4R,5S,6R)-5-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxymethyl)-6-ethyl-4-methyl-deca-2,7-dien-1-ol