62960-04-7

Basic information

• Product Name: Oxiranemethanol, 3-methyl-3-(4-methyl-3-pentenyl)-, (2R,3R)-rel-
• CAS NO: 62960-04-7
• Molecular Formula: C10H18O2
• Molecular Weight: 170.252
• Mol File: 62960-04-7.mol
• Article Data: 92

Chemical Properties

• CAS DataBase Reference: Oxiranemethanol, 3-methyl-3-(4-methyl-3-pentenyl)-, (2R,3R)-rel-(CAS DataBase Reference)
• NIST Chemistry Reference: Oxiranemethanol, 3-methyl-3-(4-methyl-3-pentenyl)-, (2R,3R)-rel-(62960-04-7)
• EPA Substance Registry System: Oxiranemethanol, 3-methyl-3-(4-methyl-3-pentenyl)-, (2R,3R)-rel-(62960-04-7)

Safety Data

• Hazardous Substances Data: 62960-04-7(Hazardous Substances Data)

Upstream product

• 443361-64-6 (3R)-(-)-3,7-dimethyl-1,2-epoxy-6-octen-3-ol 
• 106-24-1 Geraniol 
• 80037-90-7 1,1,3,3-tetramethyl-2,3-dihydro-1H-isoindol-2-yloxoyl radical 
• 104948-23-4 (2S,3R)-3-Benzyloxymethyl-2-methyl-2-(4-methyl-pent-3-enyl)-oxirane 
• 106-25-2 Nerol 
• 105929-78-0 3-methyl-3-(4-methyl-pent-3-enyl)-oxirane-2-carbaldehyde 
• 624-15-7 geraniol 
• 22410-74-8 2,7-dimethyl-2,6-octadien-1-ol 
• 141-27-5 3,7-dimethyl-2,6-octadienal 
• 16996-12-6 2,3-epoxygeranial 
• 108-05-4 vinyl acetate 

Downstream Products

• 82188-73-6 (2S,3S)-2,3-epoxygeraniol 
• 50727-94-1 (2R,3R)-3-methyl-3-(4-methyl-3-pentenyl)oxiranemethanol 
• 91048-16-7 ((2S,3S)-3-methyl-3-(4-methylpent-3-en-1-yl)oxiran-2-yl)methyl acetate 
• 131726-58-4 (2R,3R)-(3-methyl-3-(4-methylpent-3-en-1-yl)oxiran-2-yl)methyl acetate 
• 68224-83-9 (R)-3,7-dimethyloct-6-en-1-yn-3-ol 
• 29171-20-8 (S)-3,7-dimethyloct-6-en-1-yn-3-ol 
• 1514894-42-8 (4-(((2R,3R)-3-methyl-3-((R)-3-((2S,5S)-2-methyl-5-(2-((triethylsilyl)oxy)propan-2-yl)tetrahydrofuran-2-yl)-3-((triethylsilyl)oxy)propyl)oxiran-2-yl)methyl)-2-nitro-1H-pyrrol-1-yl)methyl benzoate 
• 1514894-40-6 (4-((R,Z)-3-methyl-6-((2S,5S)-2-methyl-5-(2-((triethylsilyl)oxy)propan-2-yl)tetrahydrofuran-2-yl)-6-((triethylsilyl)oxy)hex-2-en-1-yl)-2-nitro-1H-pyrrol-1-yl)methyl benzoate 
• 1515665-58-3 C₂₇H₃₈N₂O₇ 
• 1514894-35-9 1-((benzyloxy)methyl)-4-(((2R,3R)-3-methyl-3-((R)-3-((2S,5S)-2-methyl-5-(2-((triethylsilyl)oxy)propan-2-yl)tetrahydrofuran-2-yl)-3-((triethylsilyl)oxy)propyl)oxiran-2-yl)methyl)-2-nitro-1H-pyrrole 
• 1514894-33-7 1-((benzyloxy)methyl)-4-((R,Z)-3-methyl-6-((2S,5S)-2-methyl-5-(2-((triethylsilyl)oxy)propan-2-yl)tetrahydrofuran-2-yl)-6-((triethylsilyl)oxy)hex-2-en-1-yl)-2-nitro-1H-pyrrole 
• 1514894-29-1 5-(((5R)-5-((2S,5S)-2-methyl-5-(2-((triethylsilyl)oxy)propan-2-yl)tetrahydrofuran-2-yl)-5-((triethylsilyl)oxy)pentan-2-yl)thio)-1-phenyl-1H-tetrazole 
• 121693-62-7 (1S,2R,7R)-2-Benzyloxymethyl-1,6,6-trimethyl-3,5,10-trioxa-bicyclo[5.2.1]decane 
• 121693-61-6 2-[(2R,5S)-5-((R)-2-Benzyloxy-1-hydroxy-ethyl)-5-methyl-tetrahydro-furan-2-yl]-propan-2-ol 

Relevant articles and documents

Total Synthesis of Kadcoccinic Acid A Trimethyl Ester

The first total synthesis of the trimethyl ester of kadcoccinic acid A is described. The central structural element of our synthesis is a cyclopentenone motif that allows the assembly of the natural product skeleton. A gold(I)-catalyzed cyclization of an enynyl acetate led to efficient construction of the cyclopentenone scaffold. In this step, optimization studies revealed that the stereochemistry of the enynyl acetate dictates regioisomeric cyclopentenone formation. The synthesis further highlights an efficient copper-mediated conjugate addition, merged with a gold(I)-catalyzed Conia-ene reaction to connect the two fragments, thereby forging the D-ring of the natural product. The synthetic strategy reported herein can provide a general platform to access the skeleton of other members of this family of natural products.

Enantiocomplementary Epoxidation Reactions Catalyzed by an Engineered Cofactor-Independent Non-natural Peroxygenase

Peroxygenases are heme-dependent enzymes that use peroxide-borne oxygen to catalyze a wide range of oxyfunctionalization reactions. Herein, we report the engineering of an unusual cofactor-independent peroxygenase based on a promiscuous tautomerase that accepts different hydroperoxides (t-BuOOH and H2O2) to accomplish enantiocomplementary epoxidations of various α,β-unsaturated aldehydes (citral and substituted cinnamaldehydes), providing access to both enantiomers of the corresponding α,β-epoxy-aldehydes. High conversions (up to 98 %), high enantioselectivity (up to 98 % ee), and good product yields (50–80 %) were achieved. The reactions likely proceed via a reactive enzyme-bound iminium ion intermediate, allowing tweaking of the enzyme's activity and selectivity by protein engineering. Our results underscore the potential of catalytic promiscuity for the engineering of new cofactor-independent oxidative enzymes.

Total Syntheses and Determination of Absolute Configurations of Cep-212 and Cep-210, Predicted Biosynthetic Intermediates of Tetrodotoxin Isolated from Toxic Newt

Total syntheses of Cep-212 and Cep-210, predicted biosynthetic intermediates of tetrodotoxin isolated from the Japanese toxic newt, have been accomplished from geraniol by an intramolecular hetero Diels-Alder reaction as a key step in a highly stereoselective manner. The success of these syntheses enabled us to determine their absolute configurations by using a chiral normal-phase HPLC/MS analysis of the bis-dinitrobenzene derivative of natural Cep-212 and reference derivatives prepared from chemically synthesized enantiomers.