(5S,11S,13aR)-5-Benzyl-11-(6-hydroxy-oct-7-enyl)-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone

Base Information

• Chemical Name: (5S,11S,13aR)-5-Benzyl-11-(6-hydroxy-oct-7-enyl)-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone
• CAS No.: 89760-53-2
• Molecular Formula: C₂₈H₄₀N₄O₅
• Molecular Weight: 512.649
• Mol file: 89760-53-2.mol

Synonyms:

Chemical Property of (5S,11S,13aR)-5-Benzyl-11-(6-hydroxy-oct-7-enyl)-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,11S,13aR)-5-Benzyl-11-(6-hydroxy-oct-7-enyl)-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone

There total 7 articles about (5S,11S,13aR)-5-Benzyl-11-(6-hydroxy-oct-7-enyl)-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone 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: 5.0%

cyclo-(L-Ade-Aib-L-Phe-D-Pro) (89760-52-1,89826-01-7) → (5S,11S,13aR)-5-Benzyl-11-(6-hydroxy-oct-7-enyl)-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone (89760-53-2) + (5S,11S,13aR)-5-Benzyl-8,8-dimethyl-11-(6-oxo-oct-7-enyl)-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone (52574-63-7)

Guidance literature:

With tert.-butylhydroperoxide; selenium(IV) oxide; for 48h; Ambient temperature;

DOI:10.1016/S0040-4039(00)87854-5

Reference yield:

C20H35NO6 → (5S,11S,13aR)-5-Benzyl-11-(6-hydroxy-oct-7-enyl)-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone (89760-53-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 91 percent

2: 96 percent / H₂O, NaOH / acetone / 1.5 h

3: DCC / CH₂Cl₂ / 1.) 2 h, 0 deg C, 2.) 4 h, room temperature

4: CH₂Cl₂ / 0.33 h / 0 °C

5: pyridine / Ambient temperature

6: 56 percent / SeO₂, TBHP / 48 h / Ambient temperature

With pyridine; tert.-butylhydroperoxide; sodium hydroxide; selenium(IV) oxide; water; dicyclohexyl-carbodiimide; In dichloromethane; acetone;

DOI:10.1016/S0040-4039(00)87854-5

Reference yield:

1-{2-[2-(2-tert-Butoxycarbonylamino-dec-9-enoylamino)-2-methyl-propionylamino]-3-phenyl-propionyl}-pyrrolidine-2-carboxylic acid (89760-54-3) → (5S,11S,13aR)-5-Benzyl-11-(6-hydroxy-oct-7-enyl)-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone (89760-53-2)

Guidance literature:

Multi-step reaction with 4 steps

1: DCC / CH₂Cl₂ / 1.) 2 h, 0 deg C, 2.) 4 h, room temperature

2: CH₂Cl₂ / 0.33 h / 0 °C

3: pyridine / Ambient temperature

4: 56 percent / SeO₂, TBHP / 48 h / Ambient temperature

With pyridine; tert.-butylhydroperoxide; selenium(IV) oxide; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1016/S0040-4039(00)87854-5

upstream raw materials:

cyclo-(L-Ade-Aib-L-Phe-D-Pro)

1-{2-[2-(2-tert-Butoxycarbonylamino-dec-9-enoylamino)-2-methyl-propionylamino]-3-phenyl-propionyl}-pyrrolidine-2-carboxylic acid

Boc-DL-Ade-Aib-L-Phe-D-Pro-OMe

Boc-DL-Ade-Aib-L-Phe-D-Pro-OSu

Downstream raw materials:

(5S,11S,13aR)-5-Benzyl-11-(6-hydroxy-6-oxiranyl-hexyl)-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone

chlamydocin