474085-50-2

Basic information

• Product Name: (2R,3S)-3-Benzyloxy-2-[((R)-4-tert-butoxycarbonylamino-4-methoxycarbonyl-butyryl)-methyl-amino]-butyric acid benzyl ester
• Synonyms: (2R,3S)-3-Benzyloxy-2-[((R)-4-tert-butoxycarbonylamino-4-methoxycarbonyl-butyryl)-methyl-amino]-butyric acid benzyl ester
• CAS NO: 474085-50-2
• Molecular Weight: 556.656
• Mol File: 474085-50-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3S)-3-Benzyloxy-2-[((R)-4-tert-butoxycarbonylamino-4-methoxycarbonyl-butyryl)-methyl-amino]-butyric acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-3-Benzyloxy-2-[((R)-4-tert-butoxycarbonylamino-4-methoxycarbonyl-butyryl)-methyl-amino]-butyric acid benzyl ester(474085-50-2)
• EPA Substance Registry System: (2R,3S)-3-Benzyloxy-2-[((R)-4-tert-butoxycarbonylamino-4-methoxycarbonyl-butyryl)-methyl-amino]-butyric acid benzyl ester(474085-50-2)

Safety Data

• Hazardous Substances Data: 474085-50-2(Hazardous Substances Data)

Upstream product

• 35793-73-8 N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid 
• 110473-10-4 N-Boc-D-Glu α-methyl ester 
• 55227-00-4 α-Methyl (2R)-N-(tert-butoxycarbonyl)glutamate ester 

Relevant articles and documents

Enantioselective synthesis of the protein phosphatase inhibitor (-)-motuporin

A highly convergent asymmetric synthesis of the protein phosphatase inhibitor motuporin 1a is described. Synthesis and coupling of the individual peptide fragments [34 + -35 → 51] followed by macrocyclization afforded the fully protected motuporin precursor 33, which is converted to the natural product by dehydration and ester hydrolysis, Six of the eight stereogenic centers associated with the natural product were introduced using asymmetric crotylsilane bond construction methodology. Our approach features an efficient Pd(0)-catalyzed cross-coupling reaction between a configurationally well-defined vinyl zinc intermediate 22 and an (E)-vinyl iodide 7, which afforded compound 43, resulting in the construction of the trisubstituted (E,E)-diene system of the motuporin side chain. Improved reaction conditions for macrocyclization in the formation of 33 are also detailed.