94284-00-1

Upstream product

• 488-15-3 (2S,3S)-2-Hydroxy-3-methylpentanoic acid 
• 73-32-5 L-isoleucine 
• 1730-97-8 (S)-2-methylbutyraldehyde 
• 1565-80-6 (2S)-2-methyl-1-butanol 
• 56577-28-7 methyl (2S,3S)-2-hydroxy-3-methylpentanoate 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 159360-04-0 (4R,5S)-4-benzyloxycarbonylamino-5-methyl-3-oxo-heptanoic acid methyl ester 
• 159407-39-3 (3S,4R,5S)-4-benzyloxycarbonylamino-3-hydroxy-5-methyl-heptanoic acid methyl ester 
• 13139-16-7 N-tert-butoxycarbonyl-D-alloisoleucine 
• 3160-59-6 N-benzyloxycarbonylamino-D-alloisoleucine 
• 54831-20-8 (2R,3S)-2-acetamido-3-methylpentanoic acid 
• 1509-35-9 D-alloisoleucine 

Relevant academic research and scientific papers

Total synthesis of the amino hip analogue of didemnin A

Disclosed is a synthetic method for the preparation of analogs of Didemnin A (1), particularly the Amino-Hip analog of Didemnin A, also known as “AipDidemnin A” (8). These compounds have the following structures:

Synthesis of D-Alloisoleucine from L-Isoleucine and from (S)-2-Methylbutan-1-ol. Synthesis of Isostatine

Three different synthetic routes to the uncommon α-amino acid D-alloisoleucine were studied.The first was based on the stereospecific inversion of configuration of the C-2 stereogenic carbon of L-isoleucine.The second involved acetylation of L-isoleucine with epimerization at the C-2 carbon, giving a mixture of L-isoleucine and D-alloisoleucine, which was resolved enzymically with hog kidney acylase.In a new approach, an epimeric mixture of L-isoleucine and D-alloisoleucine was synthesized from (S)-2-methylbutan-1-ol and was again resolved enzymically.The D-alloisoleucine produced in these syntheses was subsequently transformed into the γ-amino acid isostatine.