30270-60-1

Basic information

• Product Name: MONOCERIN
• Synonyms: MONOCERIN;(2S)-2,3,3aα,9bα-Tetrahydro-6-hydroxy-7,8-dimethoxy-2β-propyl-5H-furo[3,2-c][2]benzopyran-5-one
• CAS NO: 30270-60-1
• Molecular Formula: C16H20O6
• Molecular Weight: 308.33
• Product Categories: Antibiotic
• Mol File: 30270-60-1.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 506.7 °C at 760 mmHg
• Flash Point: 187.5 °C
• Appearance: /
• Density: 1.235 g/cm³
• Vapor Pressure: 6.89E-11mmHg at 25°C
• Refractive Index: 1.539
• CAS DataBase Reference: MONOCERIN(CAS DataBase Reference)
• NIST Chemistry Reference: MONOCERIN(30270-60-1)
• EPA Substance Registry System: MONOCERIN(30270-60-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 30270-60-1(Hazardous Substances Data)

Usage

Definition

ChEBI: A natural product found in Colletotrichum species.

InChI:InChI=1/C16H20O6/c1-4-5-8-6-11-14(21-8)9-7-10(19-2)15(20-3)13(17)12(9)16(18)22-11/h7-8,11,14,17H,4-6H2,1-3H3/t8-,11+,14+/m0/s1

Upstream product

• 30270-61-2 (2S,3aS,9bS)-6,7,8-Trimethoxy-2-propyl-2,3,3a,9b-tetrahydro-furo[3,2-c]isochromen-5-one 
• 2305-25-1 3-hydroxy-hexanoic acid ethyl ester 
• 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 
• 66997-60-2 (+)-(3S)-3-hydroxyhexanoic acid 
• 41014-93-1 2-(S)-hydroxyvaleric acid 
• 6600-40-4 L-Norvaline 
• 29117-54-2 (S)-(-)-1,2-pentanediol 
• 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)-2,3,3a,9b,-tetrahydro-6,7,8-trimethoxy-2-propyl-5H-furol(3,2-c)⁽²⁾benzopyran-5-one 
• 3840-30-0 5-(chloromethyl)-1,2,3-trimethoxybenzene 
• 3249-68-1 ethyl butyroyl acetate 
• 3840-31-1 (3,4,5-trimethoxyphenyl)methanol 
• 123731-60-2 Methanesulfonic acid 1-(2-bromo-3,4,5-trimethoxy-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-heptyl ester 
• 123731-57-7 1-(4-t-butyldimethylsilyloxy-1-phenylthioheptyl)-3,4,5-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.