21768-33-2

Basic information

• Product Name: (2S,3R)-2-amino-4-(benzyloxy)-3-hydroxybutanoic acid
• Synonyms: (2S,3R)-2-amino-4-(benzyloxy)-3-hydroxybutanoic acid
• CAS NO: 21768-33-2
• Molecular Weight: 225.244
• Mol File: 21768-33-2.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (2S,3R)-2-amino-4-(benzyloxy)-3-hydroxybutanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-2-amino-4-(benzyloxy)-3-hydroxybutanoic acid(21768-33-2)
• EPA Substance Registry System: (2S,3R)-2-amino-4-(benzyloxy)-3-hydroxybutanoic acid(21768-33-2)

Safety Data

• Hazardous Substances Data: 21768-33-2(Hazardous Substances Data)

Upstream product

• 60656-87-3 benzyloxyacetoaldehyde 
• 56-40-6 glycine 
• 65564-05-8 3-[(benzyloxycarbonyl)amino]propanal 
• 23297-34-9 glycinate 

Downstream Products

• 1040925-48-1 C₁₂H₁₃NO₅ 
• 174713-22-5 (2S,3R)-2-[(2S,3R)-4-Benzyloxy-2-(4-benzyloxycarbonyl-butyrylamino)-3-hydroxy-butyrylamino]-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-butyric acid ethyl ester 
• 174713-21-4 (2S,3R)-2-((2S,3R)-4-Benzyloxy-2-tert-butoxycarbonylamino-3-hydroxy-butyrylamino)-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-butyric acid ethyl ester 
• 245343-34-4 (R)-3-Benzyloxycarbonylamino-N-{(1S,2R)-3-benzyloxy-2-hydroxy-1-[((3aS,5S,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl)-carbamoyl]-propyl}-succinamic acid benzyl ester 
• 245343-33-3 4-{(1S,2R)-3-Benzyloxy-2-hydroxy-1-[((3aS,5S,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl)-carbamoyl]-propylcarbamoyl}-butyric acid 
• 188825-39-0 N-{(1S,2R)-3-Benzyloxy-2-hydroxy-1-[((3aS,5S,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl)-carbamoyl]-propyl}-succinamic acid 
• 188825-35-6 {(1S,2R)-3-Benzyloxy-2-hydroxy-1-[((3aS,5S,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl)-carbamoyl]-propyl}-carbamic acid tert-butyl ester 
• 184963-20-0 (2S,3R)-2-Amino-4-benzyloxy-3-hydroxy-N-((3aS,5S,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl)-butyramide 
• 182075-77-0 (2S,3R)-4-Benzyloxy-2-(4-benzyloxycarbonyl-butyrylamino)-3-hydroxy-butyric acid 
• 215163-68-1 (2R,3S)-4-benzyloxy-3-hydroxy-2-monobenzylsuccinamidyl-butanoic acid 
• 174713-20-3 (2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyric acid 

Relevant articles and documents

An efficient chemo-enzymatic synthesis of α-amino-β-hydroxy-γ butyrolactone

The synthesis of (25,3R)-2-amino-3-hydroxybutyrolactone, a precursor of the monobactam antibiotic Carunoman, has been accomplished in three steps involving the use of L-threonine aldolase.

Enzymatic synthesis of ω-carboxy-β-hydroxy-(l)-α-amino acids

Commercially available ω-carboxy-aldehydes and glycine have been subjected to the catalytic action of an l-threonine aldolase from Escherichia coli to give the corresponding β-hydroxy-α-(l)-amino acids as a mixture of erythro/threo epimers. Specifically, the reaction with glyoxylic acid (2) gave the epimeric β-hydroxy-(l)-aspartates (t,e)-9 that could be isolated by ion-exchange chromatography in 67% yield. Following esterification and N-Boc protection, the two epimers could be isolated as pure compounds. Similarly, the aldolase-catalyzed addition of glycine to succinic semialdehyde (4) gave the expected mixture of β-hydroxy-l-α-aminoadipic acids (t)-12 and (e)-12 in 34% yield.

Kinetic and thermodynamic control of L-threonine aldolase catalyzed reaction and its application to the synthesis of mycestericin D

L-Threonine aldolase catalyzes the aldol condensation of γ-benzyloxybutanal and glycine with high erythro/threo selectivity under a kinetically controlled condition. The erythro product was used in the synthesis of mycestericin D, a potent immunosuppressant.