methyl (8R,9S,2'S,3'S,2E,4Z,6E)-8-[2'-amino-3'-phenylbutanoyloxy]-9,10-epoxy-9-methyl-2,4,6-decatrienoate

Base Information

• Chemical Name: methyl (8R,9S,2'S,3'S,2E,4Z,6E)-8-[2'-amino-3'-phenylbutanoyloxy]-9,10-epoxy-9-methyl-2,4,6-decatrienoate
• CAS No.: 247175-71-9
• Molecular Formula: C₂₂H₂₇NO₅
• Molecular Weight: 385.46
• Mol file: 247175-71-9.mol

Synonyms:methyl (8R,9S,2'S,3'S,2E,4Z,6E)-8-[2'-amino-3'-phenylbutanoyloxy]-9,10-epoxy-9-methyl-2,4,6-decatrienoate

Chemical Property of methyl (8R,9S,2'S,3'S,2E,4Z,6E)-8-[2'-amino-3'-phenylbutanoyloxy]-9,10-epoxy-9-methyl-2,4,6-decatrienoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (8R,9S,2'S,3'S,2E,4Z,6E)-8-[2'-amino-3'-phenylbutanoyloxy]-9,10-epoxy-9-methyl-2,4,6-decatrienoate

There total 5 articles about methyl (8R,9S,2'S,3'S,2E,4Z,6E)-8-[2'-amino-3'-phenylbutanoyloxy]-9,10-epoxy-9-methyl-2,4,6-decatrienoate 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: 52.0%

methyl (8R,9S,2'S,3'S,2E,4Z,6E)-9,10-epoxy-8-[2'-(9-fluorenylmethylcarbamino)-3'-phenylbutanoyloxy]-9-methyl-2,4,6-decatrienoate (247175-70-8) → methyl (8R,9S,2'S,3'S,2E,4Z,6E)-8-[2'-amino-3'-phenylbutanoyloxy]-9,10-epoxy-9-methyl-2,4,6-decatrienoate (247175-71-9)

Guidance literature:

With piperidine; In N,N-dimethyl-formamide; at 20 ℃; for 0.0833333h;

DOI:10.1271/bbb.63.1253

Reference yield:

(2S,3S)-methylphenylalanine (25488-25-9,134235-83-9) → methyl (8R,9S,2'S,3'S,2E,4Z,6E)-8-[2'-amino-3'-phenylbutanoyloxy]-9,10-epoxy-9-methyl-2,4,6-decatrienoate (247175-71-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / aq. Na₂CO₃ / dioxane / 20 °C

2: 96 percent / 4-pyrrolidinopyridine; DCC / ethyl acetate / 2 h / 20 °C

3: 52 percent / piperidine / dimethylformamide / 0.08 h / 20 °C

With piperidine; sodium carbonate; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; In 1,4-dioxane; ethyl acetate; N,N-dimethyl-formamide; 1: Condensation / 2: Condensation / 3: Hydrolysis;

DOI:10.1271/bbb.63.1253

Reference yield:

methyl (8R,9S,2E,4Z,6E)-9,10-epoxy-8-hydroxy-9-methyl-2,4,6-decatrienoate (113932-09-5) → methyl (8R,9S,2'S,3'S,2E,4Z,6E)-8-[2'-amino-3'-phenylbutanoyloxy]-9,10-epoxy-9-methyl-2,4,6-decatrienoate (247175-71-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / 4-pyrrolidinopyridine; DCC / ethyl acetate / 2 h / 20 °C

2: 52 percent / piperidine / dimethylformamide / 0.08 h / 20 °C

With piperidine; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; In ethyl acetate; N,N-dimethyl-formamide; 1: Condensation / 2: Hydrolysis;

DOI:10.1271/bbb.63.1253

upstream raw materials:

methyl (8R,9S,2'S,3'S,2E,4Z,6E)-9,10-epoxy-8-[2'-(9-fluorenylmethylcarbamino)-3'-phenylbutanoyloxy]-9-methyl-2,4,6-decatrienoate

(2S,3S)-methylphenylalanine

methyl (8R,9S,2E,4Z,6E)-9,10-epoxy-8-hydroxy-9-methyl-2,4,6-decatrienoate

N-(9-fluorenylmethoxycarbonyl)-(2S,3S)-erythro-L-β-methylphenylalanine