173327-94-1

Basic information

• Product Name: methyl (4S,2E)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate
• Synonyms: methyl (4S,2E)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate
• CAS NO: 173327-94-1
• Molecular Weight: 335.357
• Mol File: 173327-94-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: methyl (4S,2E)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (4S,2E)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate(173327-94-1)
• EPA Substance Registry System: methyl (4S,2E)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate(173327-94-1)

Safety Data

• Hazardous Substances Data: 173327-94-1(Hazardous Substances Data)

Upstream product

• 114684-69-4 methyl 2-(benzyloxycarbonylamino)-2-(diethyloxyphosphoryl)acetate 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 1191124-96-5 N-benzyloxycarbonyl-α-(diphenylphosphono)glycine methyl ester 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 100945-15-1 N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester 

Downstream Products

• 189172-25-6 (1S,2S)-1-Benzyloxycarbonylamino-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-cyclopropanecarboxylic acid methyl ester 
• 189172-26-7 (1S,2S)-1-Benzyloxycarbonylamino-2-((S)-1,2-dihydroxy-ethyl)-cyclopropanecarboxylic acid methyl ester 
• 189172-24-5 (3R,4S)-3-Benzyloxycarbonylamino-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4,5-dihydro-3H-pyrazole-3-carboxylic acid methyl ester 
• 132970-39-9 (R)-2-Benzyloxycarbonylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid methyl ester 
• 132970-38-8 methyl (2S,4R)-2-benzyloxycarbonylamino-4,5-(isopropylidenedioxy)pentanoate 

Relevant articles and documents

Stereoselective Synthesis of (E)-α,β-dehydroamino acid esters

Dehydroamino acid (Dhaa) is recognized as a useful tool or substrate for amino acid and peptide research. Although the stereoselective synthesis of the thermodynamically more stable Z-Dhaa has been well examined and established, the stereoselective synthesis of E-Dhaa has still remained to be a challenging synthetic task. In this paper, a stereoselective synthesis of E-Dhaa esters using a new (α-diphenylphosphono)glycine is described. The characteristic aspects of the new method are summarized as follows: (i) metal additives play an important role in the promotion of E-stereoselectivities. (ii) the use of NaI was effected for the synthesis of E-Dhaas bearing an aryl substituent and an amino functionality, (iii) MgBr2·OEt2 and ZnCl 2 contributed to improve the E-stereoselective synthesis of E-Dhaas bearing an alkyl substituent and an oxygen functionality, (iv) various protecting and functional groups were compatible under the reaction conditions, and (v) N-Cbz, Boc, and acyl-α-(diphenylphosphono)glycines were served for the stereoselective olefination reaction to provide the corresponding E-Dhaas. A variety of (E)-dehydroamino acid esters were stereoselectively synthesized by using (diphenylphosphono)glycinate. The stereoselectivity was influenced by metal additives. Various (E)-dehydroamino acid esters were prepared by the condensation reaction of the new phosphonates with easily available aldehydes by choosing the appropriate reaction conditions.

Amino acids and peptides; 75. Synthesis of di- and trihydroxyamino acids - Construction of lipophilic tripalmitoyldihydroxy-α-amino acids

Suitable protected derivatives of trihydroxynorleucines-[(2S,4S,5S)- and (2R,4S,5S)-2-amino-4,5,6-trihydroxyhexanoic acid], of all isomeric dihydroxynorvalines [2-amino-4,5-dihydroxypentanoic acids), of all isomeric 2-amino-6,7-dihydroxyheptanoic acids an