(2S,3R)-2-amino-4-(benzyloxy)-3-hydroxybutanoic acid

Base Information

• Chemical Name: (2S,3R)-2-amino-4-(benzyloxy)-3-hydroxybutanoic acid
• CAS No.: 21768-33-2
• Molecular Formula: C₁₁H₁₅NO₄
• Molecular Weight: 225.244
• Mol file: 21768-33-2.mol

Synonyms:(2S,3R)-2-amino-4-(benzyloxy)-3-hydroxybutanoic acid

Chemical Property of (2S,3R)-2-amino-4-(benzyloxy)-3-hydroxybutanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2-amino-4-(benzyloxy)-3-hydroxybutanoic acid

There total 6 articles about (2S,3R)-2-amino-4-(benzyloxy)-3-hydroxybutanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

benzyloxyacetoaldehyde (60656-87-3) + glycine (56-40-6,18875-39-3,25718-94-9) → (2S,3R)-2-amino-4-(benzyloxy)-3-hydroxybutanoic acid (21768-33-2) + (2S,3S)-2-amino-4-(benzyloxy)-3-hydroxybutanoic acid (102608-37-7)

Guidance literature:

With L-threonine aldolase; for 15h;

DOI:10.1016/0040-4039(96)00430-3

Reference yield: 86.0%

glycinate (23297-34-9) + benzyloxyacetoaldehyde (60656-87-3) → (2S,3R)-2-amino-4-(benzyloxy)-3-hydroxybutanoic acid (21768-33-2)

Guidance literature:

threonine-aldolase;

Reference yield: 78.0%

benzyloxyacetoaldehyde (60656-87-3) + glycine (56-40-6,18875-39-3,25718-94-9) → (2S,3R)-2-amino-4-(benzyloxy)-3-hydroxybutanoic acid (21768-33-2)

Guidance literature:

at pH 6.3 buffer, L-threonine aldolase, 1.) 30 deg C, 16 h, 2.) EtOH, 4 deg C;

DOI:10.1016/0040-4039(95)00720-W

upstream raw materials:

benzyloxyacetoaldehyde

glycine

glycinate

3-[(benzyloxycarbonyl)amino]propanal

Downstream raw materials:

C₁₂H₁₃NO₅

(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

(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

(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

Refernces

• 1、 Gutierrez, Mariana L.,Garrabou, Xavier,Agosta, Eleonora,Servi, Stefano,Parella, Teodor,Joglar, Jesus,Clapes, Pere. "Serine hydroxymethyl transferase from Streptococcus thermophilus and L-threonine aldolase from Escherichia coli as stereocomplementary biocatalysts for the synthesis of β-hydroxy-α,ω-diamino acid derivatives". experimental part. p. 4647 - 4656. Retrieved 2009/05/07.
• 2、 Kimura, Teiji,Vassilev, Vassil P.,Shen, Gwo-Jenn,Wong, Chi-Huey. "Enzymatic synthesis of β-hydroxy-α-amino acids based on recombinant D- and L-threonine aldolases". . p. 11734 - 11742. Retrieved 2007/10/03.