Nortrilobolide

Base Information

• Chemical Name: Nortrilobolide
• CAS No.: 136051-63-3
• Molecular Formula: C26H36 O10
• Molecular Weight: 508.566
• Nikkaji Number: J912.858A
• Wikidata: Q104391853
• Mol file: 136051-63-3.mol

Synonyms:nortrilobolide

Chemical Property of Nortrilobolide

Chemical Property:

• Vapor Pressure: 1.02E-16mmHg at 25°C
• Boiling Point: 596.5°Cat760mmHg
• Flash Point: 190.6°C
• PSA: 145.66000
• Density: 1.29g/cm³
• LogP: 2.04570
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 9
• Exact Mass: 508.23084734
• Heavy Atom Count: 36
• Complexity: 1030

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(=O)OC1CC(C2CC(C(=C2C3C1(C(C(=O)O3)(C)O)O)C)OC(=O)C(=CC)C)(C)OC(=O)C
• Isomeric SMILES: CCCC(=O)O[C@H]1C[C@]([C@H]2C[C@H](C(=C2[C@H]3[C@]1([C@](C(=O)O3)(C)O)O)C)OC(=O)/C(=C\C)/C)(C)OC(=O)C

Technology Process of Nortrilobolide

There total 62 articles about Nortrilobolide 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: 81.0%

(Z)-2-methyl-2-butenoic anhydride (94487-74-8) + (3S,3aR,4S,6S,6aS,8R,9bS)-6-acetoxy-3,3a,8-trihydroxy-3,6,9-trimethyl-2-oxo-2,3,3a,4,5,6,6a,7,8,9b-decahydroazuleno[4,5-b]furan-4-yl butyrate → nortrilobolide (136051-63-3)

Guidance literature:

With sodium hydrogencarbonate; at 80 ℃; for 16h;

Reference yield:

Angelic acid (565-63-9) + (3S,3aR,4S,6S,6aS,8R,9bS)-6-acetoxy-3,3a,8-trihydroxy-3,6,9-trimethyl-2-oxo-2,3,3a,4,5,6,6a,7,8,9b-decahydroazuleno[4,5-b]furan-4-yl butyrate → nortrilobolide (136051-63-3)

Guidance literature:

Angelic acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In toluene; at 20 ℃; for 1h;

(3S,3aR,4S,6S,6aS,8R,9bS)-6-acetoxy-3,3a,8-trihydroxy-3,6,9-trimethyl-2-oxo-2,3,3a,4,5,6,6a,7,8,9b-decahydroazuleno[4,5-b]furan-4-yl butyrate; In toluene; for 72h; Reflux;

Reference yield:

butanoic acid anhydride (106-31-0) + (3S,3aR,4S,6S,6aS,8R,9bS)-6-(acetyloxy)-3,3a,4-trihydroxy-3,6,9-trimethyl-2-oxo-2,3,3a,4,5,6,6a,7,8,9b-decahydroazuleno[4,5-b]furan-8-yl (2Z)-2-methylbut-2-enoate (105612-28-0) → nortrilobolide (136051-63-3)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1002/chem.200700302

upstream raw materials:

butanoic acid anhydride

(3S,3aR,4S,6S,6aS,8R,9bS)-6-(acetyloxy)-3,3a,4-trihydroxy-3,6,9-trimethyl-2-oxo-2,3,3a,4,5,6,6a,7,8,9b-decahydroazuleno[4,5-b]furan-8-yl (2Z)-2-methylbut-2-enoate

C₂₄H₄₂O₈Si₂

C₃₁H₄₂O₇Si

Downstream raw materials:

thiapsigargin

Refernces

• 1、 Chen, Dezhi,Evans, P. Andrew. "A Concise, Efficient and Scalable Total Synthesis of Thapsigargin and Nortrilobolide from (R)-(?)-Carvone". supporting information. p. 6046 - 6049. Retrieved 2017/05/09.
• 2、 Oliver, Steven F.,Hoegenauer, Klemens,Simic, Oliver,Antonello, Alessandra,Smith, Martin D.,Ley, Steven V.. "A Route to the Thapsigargins from (S)-Carvone Providing a Substrate-Controlled Total Synthesis of Trilobolide, Nortrilobolide, and Thapsivillosin F". . p. 5996 - 6000. Retrieved 2007/10/03.