107736-23-2

Basic information

• Product Name: [(2R,3R)-3-nonyloxiran-2-yl]methanol
• Synonyms: [(2R,3R)-3-nonyloxiran-2-yl]methanol
• CAS NO: 107736-23-2
• Molecular Weight: 200.321
• Mol File: 107736-23-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: [(2R,3R)-3-nonyloxiran-2-yl]methanol(CAS DataBase Reference)
• NIST Chemistry Reference: [(2R,3R)-3-nonyloxiran-2-yl]methanol(107736-23-2)
• EPA Substance Registry System: [(2R,3R)-3-nonyloxiran-2-yl]methanol(107736-23-2)

Safety Data

• Hazardous Substances Data: 107736-23-2(Hazardous Substances Data)

Upstream product

• 22104-81-0 (2E)-dodec-2-en-1-ol 
• 51148-67-5 10-undecen-1-yl p-toluenesulfonate 
• 112-38-9 10-undecenoic acid 
• 112-43-6 10-Undecen-1-ol 
• 821-95-4 1-undecene 
• 112-31-2 caprinaldehyde 

Downstream Products

• 148407-41-4 (2S-trans)-3-Nonyloxiranecarboxylic acid 
• 1387556-99-1 C₁₉H₃₁N₃O₄S 
• 1387556-98-0 (2S,3R)-2-azido-3-hydroxydodecyl 4-methylbenzenesulfonate 

Relevant articles and documents

Total synthesis and antifungal activity of (2S,3R)-2-aminododecan-3-ol

We report the total synthesis of (2S,3R)-2-aminododecan-3-ol has been achieved starting from commercially available 10-undecenoic acid. The key steps involved are Sharpless asymmetric epoxidation, Miyashita's boron-directed C-2 regioselective azidolysis, generated the asymmetric centers and in situ detosylation and reduction of azido tosylate. The antifungal activity of the synthesized (2S,3R)-2-aminododecan-3-ol was evaluated on several Candida strains and was comparable to miconazole, a standard drug.

Synthesis of the optical antipodes of 4-alkyl-γ-lactones

Optical antipodes of 4-alkyl-γ-lactones 3 have been prepared by photochemical rearrangement of optically active α,β-epoxy diazomethyl ketones 1 in ethanol to give 4-hydroxy-alkenoates 2, followed by reduction of the alkene bond and subsequent lactonization.The required epoxy diazomethyl ketones 1 were obtained via the following sequence of reactions: alkylation of 2-propyn-1-ol, subsequent reduction to the alkenols 6, Sharpless epoxidation to 2,3-epoxy alcohols 7, oxidation to glycidic esters 8 and finally conversion to diazo ketones 1.The enantiomeric purities range from 84 to 100percent.