(2E,4E,6E)-(R)-8-((S)-2-Acetylamino-3-phenyl-propionyloxy)-8-((R)-2-methyl-oxiranyl)-octa-2,4,6-trienoic acid methyl ester

Base Information

• Chemical Name: (2E,4E,6E)-(R)-8-((S)-2-Acetylamino-3-phenyl-propionyloxy)-8-((R)-2-methyl-oxiranyl)-octa-2,4,6-trienoic acid methyl ester
• CAS No.: 104855-38-1
• Molecular Formula: C₂₃H₂₇NO₆
• Molecular Weight: 413.47
• Mol file: 104855-38-1.mol

Synonyms:

Chemical Property of (2E,4E,6E)-(R)-8-((S)-2-Acetylamino-3-phenyl-propionyloxy)-8-((R)-2-methyl-oxiranyl)-octa-2,4,6-trienoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4E,6E)-(R)-8-((S)-2-Acetylamino-3-phenyl-propionyloxy)-8-((R)-2-methyl-oxiranyl)-octa-2,4,6-trienoic acid methyl ester

There total 110 articles about (2E,4E,6E)-(R)-8-((S)-2-Acetylamino-3-phenyl-propionyloxy)-8-((R)-2-methyl-oxiranyl)-octa-2,4,6-trienoic acid methyl ester 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:

4-(tert-Butyldiphenylsiloxy)-5-methylhexa-2(E),5-dienal (104840-65-5) → (2E,4E,6E)-(R)-8-((S)-2-Acetylamino-3-phenyl-propionyloxy)-8-((R)-2-methyl-oxiranyl)-octa-2,4,6-trienoic acid methyl ester (104855-38-1,104973-55-9,104973-56-0,104973-57-1,114028-37-4,114029-76-4,130323-47-6,130466-12-5)

Guidance literature:

Multi-step reaction with 7 steps

1: sodium hydride

2: DIBAH

3: MnO₂

4: sodium hydride

5: m-chloroperbenzoic acid

6: tetrabutylammonium fluoride

7: dicyclohexylcarbodiimide, 4-pyrrolidinopyridine / CH₂Cl₂

With manganese(IV) oxide; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; 4-pyrrolidin-1-ylpyridine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1248/cpb.34.2668

Reference yield:

Methyl 4-(tert-Butyldiphenylsiloxy)-5-methyl-hexa-2(E),5-dienoate (104840-63-3) → (2E,4E,6E)-(R)-8-((R)-2-Acetylamino-3-phenyl-propionyloxy)-8-((S)-2-methyl-oxiranyl)-octa-2,4,6-trienoic acid methyl ester (104855-38-1,104973-55-9,104973-56-0,104973-57-1,114028-37-4,114029-76-4,130323-47-6,130466-12-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 95 percent / DIBAH

2: 92 percent / MnO₂

3: sodium hydride

4: DIBAH

5: MnO₂

6: sodium hydride

7: m-chloroperbenzoic acid

8: tetrabutylammonium fluoride

9: dicyclohexylcarbodiimide, 4-pyrrolidinopyridine / CH₂Cl₂

With manganese(IV) oxide; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; 4-pyrrolidin-1-ylpyridine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1248/cpb.34.2668

Reference yield:

4-(tert-Butyldiphenylsiloxy)-5-methylhexa-2(E),5-dien-1-ol (104840-64-4) → (2E,4E,6E)-(R)-8-((R)-2-Acetylamino-3-phenyl-propionyloxy)-8-((S)-2-methyl-oxiranyl)-octa-2,4,6-trienoic acid methyl ester (104855-38-1,104973-55-9,104973-56-0,104973-57-1,114028-37-4,114029-76-4,130323-47-6,130466-12-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 92 percent / MnO₂

2: sodium hydride

3: DIBAH

4: MnO₂

5: sodium hydride

6: m-chloroperbenzoic acid

7: tetrabutylammonium fluoride

8: dicyclohexylcarbodiimide, 4-pyrrolidinopyridine / CH₂Cl₂

With manganese(IV) oxide; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; 4-pyrrolidin-1-ylpyridine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1248/cpb.34.2668

upstream raw materials:

(S)-2-acetylamino-3-phenylpropanoic acid

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

2-(tert-Butyldiphenylsiloxy)-3-methyl-but-3-enal

4-(tert-Butyldiphenylsiloxy)-5-methylhexa-2(E),5-dienal

Refernces

• 1、 Irie,Matsumoto,Kitagawa,Zhang,Ueno,Nakashima,Fukami. "Total synthesis of esters of AK-toxin II and AF-toxin IIc starting from vitamin C as a chiral material". . p. 2598 - 2601. Retrieved 2007/10/02.