1-Oxa-4-azacyclotridec-9-ene-2,5-dione, 13-(4-hydroxybutyl)-4,6,8,11-tetramethyl-3-(phenylmethyl)-, (3S,6R,8S,9Z,11S,13R)-

Base Information

• Chemical Name: 1-Oxa-4-azacyclotridec-9-ene-2,5-dione, 13-(4-hydroxybutyl)-4,6,8,11-tetramethyl-3-(phenylmethyl)-, (3S,6R,8S,9Z,11S,13R)-
• CAS No.: 723296-19-3
• Molecular Formula: C26H39NO4
• Molecular Weight: 429.6
• Mol file: 723296-19-3.mol

Synonyms:

Chemical Property of 1-Oxa-4-azacyclotridec-9-ene-2,5-dione, 13-(4-hydroxybutyl)-4,6,8,11-tetramethyl-3-(phenylmethyl)-, (3S,6R,8S,9Z,11S,13R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Oxa-4-azacyclotridec-9-ene-2,5-dione, 13-(4-hydroxybutyl)-4,6,8,11-tetramethyl-3-(phenylmethyl)-, (3S,6R,8S,9Z,11S,13R)-

There total 13 articles about 1-Oxa-4-azacyclotridec-9-ene-2,5-dione, 13-(4-hydroxybutyl)-4,6,8,11-tetramethyl-3-(phenylmethyl)-, (3S,6R,8S,9Z,11S,13R)- 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: 93.0%

(Z)-(3S,6R,8S,11S,13R)-3-Benzyl-13-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-4,6,8,11-tetramethyl-1-oxa-4-aza-cyclotridec-9-ene-2,5-dione (723296-12-6) → (Z)-(3S,6R,8S,11S,13R)-3-Benzyl-13-(4-hydroxy-butyl)-4,6,8,11-tetramethyl-1-oxa-4-aza-cyclotridec-9-ene-2,5-dione (723296-19-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1021/ol061029w

Reference yield:

5-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-3-methyl-tetrahydro-furan-2-ol → (Z)-(3S,6R,8S,11S,13R)-3-Benzyl-13-(4-hydroxy-butyl)-4,6,8,11-tetramethyl-1-oxa-4-aza-cyclotridec-9-ene-2,5-dione (723296-19-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 289 mg / n-BuLi / tetrahydrofuran; hexane / 3 h / 20 °C

2: 67 percent / triphenylphosphine; DIAD / diethyl ether / 1.5 h / 20 °C

3: TFA / CH₂Cl₂ / 1 h / 0 °C

4: 141 mg / HOBt; EDCI / CH₂Cl₂ / 6 h / 20 °C

5: 93 percent / Grubb's catalyst 2nd generation / CH₂Cl₂ / Heating

6: 93 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

With n-butyllithium; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; trifluoroacetic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1: Wittig reaction / 2: Mitsunobu reaction;

DOI:10.1021/ol061029w

Reference yield:

1-(tert-butyldiphenylsilyloxy)-7-methyl-non-8-en-5-ol (723296-06-8) → (Z)-(3S,6R,8S,11S,13R)-3-Benzyl-13-(4-hydroxy-butyl)-4,6,8,11-tetramethyl-1-oxa-4-aza-cyclotridec-9-ene-2,5-dione (723296-19-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 67 percent / triphenylphosphine; DIAD / diethyl ether / 1.5 h / 20 °C

2: TFA / CH₂Cl₂ / 1 h / 0 °C

3: 141 mg / HOBt; EDCI / CH₂Cl₂ / 6 h / 20 °C

4: 93 percent / Grubb's catalyst 2nd generation / CH₂Cl₂ / Heating

5: 93 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

With di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; trifluoroacetic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; 1: Mitsunobu reaction;

DOI:10.1021/ol061029w

upstream raw materials:

(Z)-(3S,6R,8S,11S,13R)-3-Benzyl-13-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-4,6,8,11-tetramethyl-1-oxa-4-aza-cyclotridec-9-ene-2,5-dione

Methanesulfonic acid (1S,2R)-1-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2-methyl-but-3-enyl ester

1-(tert-butyldiphenylsilyloxy)-7-methyl-non-8-en-5-ol

2-(tert-butoxycarbonyl-methyl-amino)-3-phenyl-propionic acid 1-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-3-methyl-pent-4-enyl ester

Downstream raw materials:

4-((3S,6R,8R,11R,13R)-3-Benzyl-4,6,8,11-tetramethyl-2,5-dioxo-1-oxa-4-aza-cyclotridec-13-yl)-butyraldehyde

(3S,6R,8R,11R,13R)-3-benzyl-13-(4-hydroxy-butyl)-4,6,8,11-tetramethyl-1-oxa-4-azacyclotridecane-2,5-dione