(+)-macrosphelide B

Base Information

• Chemical Name: (+)-macrosphelide B
• CAS No.: 172923-78-3
• Molecular Formula: C16H20 O8
• Molecular Weight: 340.33
• DSSTox Substance ID: DTXSID801043578
• Nikkaji Number: J919.817B
• Wikidata: Q44186030

Synonyms:(+)-macrosphelide B;172923-78-3;DTXSID801043578;Q44186030;(4S,7E,9R,10S,13E,16S)-9-hydroxy-4,10,16-trimethyl-1,5,11-trioxacyclohexadeca-7,13-diene-2,6,12,15-tetrone

Chemical Property of (+)-macrosphelide B

Chemical Property:

• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 0
• Exact Mass: 340.11581759
• Heavy Atom Count: 24
• Complexity: 562

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(=O)OC(C(=O)C=CC(=O)OC(C(C=CC(=O)O1)O)C)C
• Isomeric SMILES: C[C@H]1CC(=O)O[C@H](C(=O)/C=C/C(=O)O[C@H]([C@@H](/C=C/C(=O)O1)O)C)C

Technology Process of (+)-macrosphelide B

There total 1 articles about (+)-macrosphelide B 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: 36.0%

(+)-macrosphelide A (172923-77-2) → (3S,9S,15S)-(6E,12E)-3,9,15-trimethyl-4,10,16-trioxacyclohexadeca-6,12-diene-1,5,8,11,14-pentone + (5R,6S,12S,16S)-(3E,9E)-5-hydroxy-6,12,16-trimethyl-1,7,13-trioxacyclohexadeca-3,9-diene-2,8,11,14-tetraone (172923-78-3) + (4S,7E,10S,13E,15R,16S)-15-hydroxy-4,10,16-trimethyl-1,5,11-trioxacyclohexadeca-7,13-diene-2,6,9,12-tetraone

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at -20 ℃; for 6h; chemoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.joc.5b01171

Reference yield:

(5R,6S,12S,16S)-(3E,9E)-5-hydroxy-6,12,16-trimethyl-1,7,13-trioxacyclohexadeca-3,9-diene-2,8,11,14-tetraone (172923-78-3) → (+)-macrosphelide A (172923-77-2) + 14-epi macrosphelide A

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 1h; Title compound not separated from byproducts.;

DOI:10.1021/jo001495d

Reference yield:

(5R,6S,12S,16S)-(3E,9E)-5-hydroxy-6,12,16-trimethyl-1,7,13-trioxacyclohexadeca-3,9-diene-2,8,11,14-tetraone (172923-78-3) → (+)-macrosphelide A (172923-77-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 75 percent / (i-Pr)2NEt / CH₂Cl₂ / 60 h / 20 °C

2.1: 74 percent / NaBH₄ / methanol / 0.33 h / -15 °C

3.1: HCO₂H; DEAD; PPh₃ / tetrahydrofuran / 1.5 h / 20 °C

3.2: 72 percent / Et₃N / methanol / 1 h / 20 °C

4.1: 70 percent / CF₃CO₂H / CH₂Cl₂ / 2 h / 20 °C

With sodium tetrahydroborate; formic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; 3.1: Mitsunobu reaction / 3.2: Mitsunobu reaction;

DOI:10.1021/jo001495d

upstream raw materials:

(+)-macrosphelide A

Downstream raw materials:

(+)-macrosphelide A

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