Aids033397

Base Information

• Chemical Name: Aids033397
• CAS No.: 183904-54-3
• Molecular Formula: C22H24O5
• Molecular Weight: 368.423
• Mol file: 183904-54-3.mol

Synonyms:2',3'-h]chromene-2,12-dione;(10S,11S)-6,6,10,11-Tetramethyl-4-propyl-10,11-dihydro-6H-dipyrano[2,3-f;

Chemical Property of Aids033397

Chemical Property:

• Boiling Point: 546.7°Cat760mmHg
• Flash Point: 298.4°C
• PSA: 65.74000
• Density: 1.176g/cm³
• LogP: 4.52940

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Aids033397

There total 11 articles about Aids033397 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: 61.0%

(-)-calanolide B (909-14-8) → (10S,11S)-10,11-dihydro-4-propyl-6,6,10,11-tetramethyl-2H,6H,12H-benzo[1,2-b;3,4-b';5,6-b'']tripyran-2,12-dione (183904-54-3,161753-49-7)

Guidance literature:

With jones reagent; In acetone; at 0 ℃; for 0.833333h;

DOI:10.1021/jm9602827

Reference yield:

(+/-)-Calanolide A → (10S,11S)-10,11-dihydro-4-propyl-6,6,10,11-tetramethyl-2H,6H,12H-benzo[1,2-b;3,4-b';5,6-b'']tripyran-2,12-dione (183904-54-3,161753-49-7)

Guidance literature:

Multi-step reaction with 2 steps

1: Jones reagent / acetone / 0 °C

With jones reagent; In acetone;

DOI:10.1021/jm9602827

Reference yield:

(8R,9S)-8,9-dihydro-8,9-dimethyl-5-methoxy-4-propyl-2H,10H-benzo[1,2-b;5,6-b']dipyran-2,10-dione (334881-61-7) → (10S,11S)-10,11-dihydro-4-propyl-6,6,10,11-tetramethyl-2H,6H,12H-benzo[1,2-b;3,4-b';5,6-b'']tripyran-2,12-dione (183904-54-3,161753-49-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / MgI₂; K₂CO₃ / benzene / 360 h / Heating

2: phenylboronic acid; propionic acid / toluene / 1.5 h / Heating

With potassium carbonate; propionic acid; magnesium iodide; phenylboronic acid; In toluene; benzene;

upstream raw materials:

(+/-)-12-oxocalanolide A

(-)-calanolide B

5-Hydroxy-6-((2R,3S)-3-hydroxy-2-methyl-butyryl)-2,2-dimethyl-10-propyl-2H-pyrano[2,3-f]chromen-8-one

5-Hydroxy-6-((2R,3R)-3-hydroxy-2-methyl-butyryl)-2,2-dimethyl-10-propyl-2H-pyrano[2,3-f]chromen-8-one

Downstream raw materials:

7,8-dihydro-(-)-calanolide B

Refernces

• 1、 Tanaka, Tomohiro,Kumamoto, Takuya,Ishikawa, Tsutomu. "Enantioselective total synthesis of anti HIV-1 active (+)-calanolide A through a quinine-catalyzed asymmetric intramolecular oxo-Michael addition". . p. 10229 - 10232. Retrieved 2007/10/03.
• 2、 Khilevich, Albert,Mar, Aye,Flavin, Michael T.,Rizzo, John D.,Lin, Lin,Dzekhtser, Sergey,Brankovic, Darko,Zhang, Heping,Chen, Wei,Liao, Shuyuan,Zembower, David E.,Xu, Ze-Qi. "Synthesis of (+)-calanolide A, an anti-HIV agent, via enzyme-catalyzed resolution of the aldol products". . p. 3315 - 3326. Retrieved 2007/10/03.