1434563-90-2

Basic information

• Product Name: (2S,4E)-1-benzyl-2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)amino]-6-methylhex-4-enedioate
• Synonyms: (2S,4E)-1-benzyl-2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)amino]-6-methylhex-4-enedioate
• CAS NO: 1434563-90-2
• Molecular Weight: 527.69
• Mol File: 1434563-90-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,4E)-1-benzyl-2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)amino]-6-methylhex-4-enedioate(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4E)-1-benzyl-2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)amino]-6-methylhex-4-enedioate(1434563-90-2)
• EPA Substance Registry System: (2S,4E)-1-benzyl-2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)amino]-6-methylhex-4-enedioate(1434563-90-2)

Safety Data

• Hazardous Substances Data: 1434563-90-2(Hazardous Substances Data)

Upstream product

• 162398-42-7 (E)-benzyl 4-oxobut-2-enoate 
• 1434564-22-3 (2E)-benzyl 4,4-dimethoxybut-2-enoate 
• 7396-44-3 benzyl diethylphosphonoacetate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 3426-71-9 Benzyl N-hydroxycarbamate 
• 909019-16-5 benzyl (tert‐butyldimethylsilyl)oxycarbamate 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 1434564-64-3 (3S,5R)-benzyl-5-[(methoxycarbonyl)methyl]-3-benzyloxycarbonylisooxazolidine-2-carboxylate 

Relevant articles and documents

Synthesis of orthogonally protected (2S)-2-amino-adipic acid (α-AAA) and (2S,4 R)-2-amino-4-hydroxyadipic acid (Ahad)

(2S,4R)-2-Amino-4-hydroxyadipic acid (Ahad) building block 45 was synthesized in 11 steps and 6.5% overall yield from commercially available materials. Key steps in stereocontrol were an asymmetric conjugate addition employing a proline-based catalyst and a syn-selective intramolecular-conjugate addition of an oxygen nucleophile to an α,β-unsaturated ester. To enable incorporation of α-amino-adipic acid (α-AAA) and Ahad into peptides, a truly orthogonal protecting group scheme was developed, encompassing an allyloxycarbonyl (Alloc) carbamate for Nα, a tert-butyl ester for the δ-COOH, an acetol ester for the α-COOH, and a tert- butyldimethylsilyl ether for the γ-hydroxy group of Ahad.