76023-57-9

Basic information

• Product Name: grahamimycin A
• Synonyms: grahamimycin A
• CAS NO: 76023-57-9
• Molecular Formula: C14H18O6
• Molecular Weight: 282.29
• Mol File: 76023-57-9.mol

Chemical Properties

• Boiling Point: 546.3°C at 760 mmHg
• Flash Point: 206.4°C
• Appearance: /
• Density: 1.159g/cm³
• Vapor Pressure: 3.27E-14mmHg at 25°C
• Refractive Index: 1.479
• CAS DataBase Reference: grahamimycin A(CAS DataBase Reference)
• NIST Chemistry Reference: grahamimycin A(76023-57-9)
• EPA Substance Registry System: grahamimycin A(76023-57-9)

Safety Data

• Hazardous Substances Data: 76023-57-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H18O6/c1-9-4-3-5-13(17)20-10(2)8-12(16)11(15)6-7-14(18)19-9/h3,5-7,9-10,12,16H,4,8H2,1-2H3/b5-3-,7-6-/t9-,10+,12-/m1/s1

Upstream product

• 91273-95-9 (3E,6R,9E,11R,12R,14R)-11,12-(isopropylidenedioxy)-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione 
• 116908-88-4 (2E,4R,5R,7R,10E,13R)-13-hydroxy-4,5-(isopropylidenedioxy)-7-methyl-9-oxo-8-oxatetradeca-2,10-dienoic acid 
• 133522-13-1 (5R,2E)-5-(tert-butyl-dimethyl-silyloxy)-hex-2-enoic acid 
• 307298-68-6 (1'R,3'R)-3'-(2-furyl)-3'-methoxymethyloxy-1'-methylpropyl (5R,2E)-5-tetrahydropyranyloxy-2-hexenoate 
• 307298-59-5 (1'R,3'R)-3'-(2-furyl)-3'-methoxymethyloxy-1'-methylpropyl (5R,2E)-5-hydroxy-2-hexenoate 
• 307298-63-1 (1R,3R)-1-(2-furyl)-1-methoxymethyloxy-3-tetrahydropyranyloxybutane 
• 307298-62-0 (1R,3R)-1-(2-furyl)-3-tetrahydropyranyloxy-1-butanol 
• 307298-61-9 (3R)-1-(2-furyl)-3-tetrahydropyranyloxy-1-butanol 
• 307298-60-8 (2R,4R)-4-(furan-2-yl)-4-(methoxymethoxy)butan-2-ol 
• 90503-13-2 (2E,5R)-5-(Tetrahydropyran-2-yloxy)hex-2-enoic acid 
• 77286-11-4 Ethyl (2E,5R)-5-(tetrahydropyran-2-yloxy)hex-2-enoate 
• 485323-96-4 (E)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-hex-2-enoic acid (R)-2-[(4R,5R)-5-((E)-2-methoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-1-methyl-ethyl ester 
• 485323-94-2 (E)-(R)-5-Hydroxy-hex-2-enoic acid (R)-2-[(4R,5R)-5-((E)-2-methoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-1-methyl-ethyl ester 
• 485323-93-1 (4R,5R,7R)-7-(tert-butyl-dimethyl-silyloxy)-4,5-dihydroxy-oct-2-enoic acid methyl ester 

Downstream Products

• 74838-13-4 (-)-grahamimycin A₁ 

Relevant articles and documents

Enantioselective syntheses of colletodiol, colletol, and grahamimycin A.

[reaction: see text] The enantioselective synthesis of colletodiol has been achieved in 11 steps from methyl 1,3,5-octatrienoate and 16 total steps from both ethyl sorbate and methyl 1,3,5-octatrienoate. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form a 5-hydroxy-1-enoate and an 7-hydroxy-1,3-dienoate. These esters were further functionalized, coupled, and macrolactonized to provide colletodiol after deprotection. Grahamimycin A and colletol were synthesized in one and two steps, respectively, from colletodiol.