28890-33-7

Basic information

• Product Name: (2R,3aR,9bR)-2,3,3a,9b-tetrahydro-6-hydroxy-7,8-dimethoxy-2-propyl-5H-furo(3,2-c)(2)benzopyran-5-one
• CAS NO: 28890-33-7
• Molecular Weight: 308.331
• Mol File: 28890-33-7.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (2R,3aR,9bR)-2,3,3a,9b-tetrahydro-6-hydroxy-7,8-dimethoxy-2-propyl-5H-furo(3,2-c)(2)benzopyran-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3aR,9bR)-2,3,3a,9b-tetrahydro-6-hydroxy-7,8-dimethoxy-2-propyl-5H-furo(3,2-c)(2)benzopyran-5-one(28890-33-7)
• EPA Substance Registry System: (2R,3aR,9bR)-2,3,3a,9b-tetrahydro-6-hydroxy-7,8-dimethoxy-2-propyl-5H-furo(3,2-c)(2)benzopyran-5-one(28890-33-7)

Safety Data

• Hazardous Substances Data: 28890-33-7(Hazardous Substances Data)

Upstream product

• 30270-61-2 (2S,3aS,9bS)-2,3,3a,9b,-tetrahydro-6,7,8-trimethoxy-2-propyl-5H-furol(3,2-c)⁽²⁾benzopyran-5-one 
• 41014-93-1 2-(S)-hydroxyvaleric acid 
• 66997-60-2 (+)-(3S)-3-hydroxyhexanoic acid 
• 30270-61-2 (2S,3aR,9bR)-2,3,3a,9b-tetrahydro-6,7,8-trimethoxy-2-propyl-5H-furol(3,2-c)⁽²⁾benzopyran-5-one 
• 1360789-71-4 methyl 2-acetoxy-6-((S,E)-4-(tert-butyldimethylsilyloxy)hept-1-enyl)-3,4-dimethoxybenzoate 
• 1360789-77-0 (2S,3aR,9bR)-6-acetoxy-7,8-dimethoxy-2-propyl-2,3,3a,9b-tetrahydro-5H-furo[3,2-c][2]benzopyran-5-one 
• 1360789-67-8 methyl 2-hydroxy-6-iodo-3,4-dimethoxybenzoate 
• 1752-02-9 methyl 6-iodo-2,3,4-trimethoxybenzoate 
• 3521-91-3 (4R)-hept-1-en-ol 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 73252-53-6 3,4,5-trimethoxy-2-iodobenzaldehyde 
• 30270-61-2 (2S*,3aR*,9bR*)-2,3,3a,9b-tetrahydro-6,7,8-trimethoxy-2-propyl-5H-furol(3,2-c)⁽²⁾benzopyran-5-one 
• 30270-61-2 (2S,3aS,9bS)-6,7,8-Trimethoxy-2-propyl-2,3,3a,9b-tetrahydro-furo[3,2-c]isochromen-5-one 
• 3840-30-0 5-(chloromethyl)-1,2,3-trimethoxybenzene 

Relevant articles and documents

Enantioselective Total Synthesis of (+)-Monocerin, a Dihydroisocoumarin Derivative with Potent Antimalarial Properties

We describe here the enantioselective synthesis of (+)-monocerin and its acetate derivative. The present synthesis features an efficient optically active synthesis of the β-hydroxy-?-lactone derivative with high enantiomeric purity using Sharpless dihydroxylation as the key step. The synthesis also highlights a tandem Lewis acid-catalyzed, oxocarbenium ion-mediated diastereoselective syn-allylation reaction, and a methoxymethyl group promoted methylenation reaction. We investigated this reaction with a variety of Lewis acids. A selective CrO3-mediated oxidation of isochroman provided the corresponding lactone derivative. The synthesis is quite efficient and may be useful for the preparation of derivatives.

Total synthesis of (+)-monocerin via tandem dihydroxylation-SN2 cyclization and a copper mediated tandem cyanation-lactonization approach

A simple and novel synthesis of (+)-monocerin was achieved in 15 steps and 15.5% overall yield from 3-buten-1-ol employing hydrolytic kinetic resolution, Julia olefination, intramolecular tandem Sharpless asymmetric dihydroxylation-SN2 cyclizat

Asymmetric total synthesis of fusarentin 6-methyl ether and its biomimetic transformation into fusarentin 6,7-dimethyl ether, 7-O-demethylmonocerin, and (+)-monocerin

A concise asymmetric total synthesis of a fusarentin ether (1) with sequential biomimetic transformation to its analogues fusarentin 6,7-dimethyl ether (2), 7-O-demethylmonocerin (3), and (+)-monocerin (4) has been accomplished. The cis-fused furobenzopyranones of 7-O-demethylmonocerin (3) and (+)-monocerin (4) were efficiently constructed via an intramolecular nucleophilic trapping of a quinonemethide intermediate, which was obtained by benzylic oxidation of fusarentin 6-methyl ether (1) using hypervalent iodine reagent.