205584-90-3

Basic information

• Product Name: Naphthalene-1-carboxylic acid (S)-benzyloxycarbonyl-((S)-2-methyl-oxiranyl)-methyl ester
• Synonyms: Naphthalene-1-carboxylic acid (S)-benzyloxycarbonyl-((S)-2-methyl-oxiranyl)-methyl ester
• CAS NO: 205584-90-3
• Molecular Weight: 376.409
• Mol File: 205584-90-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Naphthalene-1-carboxylic acid (S)-benzyloxycarbonyl-((S)-2-methyl-oxiranyl)-methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Naphthalene-1-carboxylic acid (S)-benzyloxycarbonyl-((S)-2-methyl-oxiranyl)-methyl ester(205584-90-3)
• EPA Substance Registry System: Naphthalene-1-carboxylic acid (S)-benzyloxycarbonyl-((S)-2-methyl-oxiranyl)-methyl ester(205584-90-3)

Safety Data

• Hazardous Substances Data: 205584-90-3(Hazardous Substances Data)

Upstream product

• 157087-28-0 (S)-benzyl 2-hydroxy-3-methylbut-3-enoate 
• 205584-89-0 (S)-benzyl 3,3-dimethyloxirane-2-carboxylate 
• 184528-78-7 (R)-1-((benzyloxy)carbonyl)-2-hydroxy-2-methylpropyl methanesulfonate 
• 184528-76-5 (R)-benzyl 2,3-dihydroxy-3-methylbutanoate 
• 100-39-0 benzyl bromide 
• 37526-89-9 benzyl 3-methylbut-2-enoate 
• 541-47-9 3-Methylbutenoic acid 
• 127661-25-0 (S)-benzyl 2-hydroxy-2-((S)-2-methyloxiran-2-yl)acetate 
• 879-18-5 naphthalene-1-carbonic acid chloride 

Relevant articles and documents

Delineating noncovalent interactions between the azinomycins and double-stranded DNA: Importance of the naphthalene substitution pattern on interstrand cross-linking efficiency

(Chemical Equation Presented) Using a series of synthetic azinomycin analogues, it is shown that the efficiency of in vitro DNA interstrand cross-linking is markedly reduced when either the C-5′ methyl group or both the C-5′ methyl and C-3′ methoxy groups

Asymmetric synthesis of the left hand portion of the azinomycins

A nine step synthesis of the left hand portion of the azinomycins is described starting from 3,3-dimethyl-acrylic acid. The approach relies on a Sharpless asymmetric dihydroxylation (AD) reaction to install the requisite (2S,3S)-stereochemistry of epoxy alcohol 4. This epoxide is converted to crystalline amide derivative 12 whose structure and absolute stereochemistry have been unambiguously established using X-ray crystallography. Coupling of epoxy alcohol (2S,3S)-4 with naphthoyl chloride 16 and subsequent manipulations furnish epoxy amide (2S,3S)-1 identical in all respects with the natural material.