49705-98-8

Basic information

• Product Name: Benzyl (2R,3S)-(1-carbamoyl-2-hydroxypropyl)carbamate
• Synonyms: N-Benzyloxycarbonyl-L-Threoninamide;benzyl [R-(R*,S*)]-(1-carbamoyl-2-hydroxypropyl)carbamate;CBZTA;[(2R,3S)-1-Amino-3-hydroxy-1-oxo-2-(phenylmethyl)butan-2-yl] carbamate;Benzyl (2R,3S)-(1-carbamoyl-2-hydroxypropyl)carbamate;CBZ-L-THREONINE AMIDE;N-Carbobenzyloxy-L-threoninamide;N2-(Benzyloxycarbonyl)-L-threoninamide
• CAS NO: 49705-98-8
• Molecular Formula: C₁₂H₁₆N₂O₄
• Molecular Weight: 252.27
• EINECS: 256-436-9
• Product Categories: Threonine [Thr, T]
• Mol File: 49705-98-8.mol

Chemical Properties

• Boiling Point: 508.4 °C at 760 mmHg
• Flash Point: 261.3 °C
• Appearance: White/Powder
• Density: 1.263 g/cm³
• Vapor Pressure: 2.07E-13mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slig
• PKA: 10.96±0.46(Predicted)
• BRN: 2335408
• CAS DataBase Reference: Benzyl (2R,3S)-(1-carbamoyl-2-hydroxypropyl)carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl (2R,3S)-(1-carbamoyl-2-hydroxypropyl)carbamate(49705-98-8)
• EPA Substance Registry System: Benzyl (2R,3S)-(1-carbamoyl-2-hydroxypropyl)carbamate(49705-98-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 49705-98-8(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Threonine

InChI:InChI=1/C12H16N2O4/c1-8(15)12(10(13)16,18-11(14)17)7-9-5-3-2-4-6-9/h2-6,8,15H,7H2,1H3,(H2,13,16)(H2,14,17)/t8-,12+/m0/s1

Upstream product

• 57224-63-2 methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate 
• 19728-63-3 N-benzyloxycarbonyl-L-treonine 
• 501-53-1 benzyl chloroformate 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 33209-01-7 L-threonine amide hydrochloride 
• 49705-99-9 (2S,3R)-2-amino-3-hydroxybutanamide 

Downstream Products

• 49705-99-9 (2S,3R)-2-amino-3-hydroxybutanamide 
• 131458-44-1 benzyl (carbamoylcarbonyl)carbamate 
• 185950-45-2 N-benzyloxycarbonyl-L-3-O-(t-butyldimethylsilyl)threoninamide 
• 213695-83-1 (2S,3R)-2-benzyloxycarbonylamino-3-(t-butyldiphenylsiloxy)butanamide 
• 1621581-71-2 (2R,3S)-4-amino-3-(((benzyloxy)carbonyl)amino)-4-oxobutan-2-yl acetate 
• 80082-51-5 N-benzyloxycarbonyl-O-methanesulfonyl-L-threonine amide 
• 115887-91-7 (3S,4R)-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt 
• 33209-01-7 L-threonine amide hydrochloride 

Relevant articles and documents

In vitro synthesis of mucin-type O-glycans using saccharide primers comprising GalNAc-Ser and GalNAc-Thr residues

Mucin-type O-glycosylation of serine or threonine residue in proteins is known to be one of the major post-translational modifications. In this study, two novel alkyl glycosides, Nα-lauryl-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serineamide (GalNAc-Ser-C12) and Nα-lauryl-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonineamide (GalNAc-Thr-C12) were synthesized as saccharide primers to prime mucin-type O-glycan biosynthesis in cells. Upon incubating human gastric cancer MKN45 cells with the saccharide primers, 22 glycosylated products were obtained, and their structures were analyzed using liquid chromatography-mass spectrometry and enzyme digestion. The amounts of glycosylated products were dependent on the amino acid residues in the saccharide primers. For example, in vitro synthesis of T antigen (Galβ1-3GalNAc), fucosyl-T (Fucα1-2Galβ1-3GalNAc), and sialyl-T (NeuAcα2-3Galβ1-3GalNAc) preferred a serine residue, whereas sialyl-Tn (NeuAcα2-6GalNAc) preferred a threonine residue. Furthermore, the glycosylated products derived from GalNAc-Ser/Thr-C12 and Gal-GalNAc-Ser/Thr-C12 using cell-free synthesis showed the same amino acid selectivity as those in the cell experiments. These results indicate that glycosyltransferases involved in the biosynthesis of mucin-type O-glycans distinguish amino acid residues conjugated to GalNAc. The saccharide primers developed in this study might be useful for comparing mucin-type oligosaccharides in cells and constructing oligosaccharide libraries to study cell function.

Ammonia curved the monocyclic parent nucleus method for the preparation of

The invention relates to a preparation of Aztreonam monocyclic parent nucleus method, in the method using benzyl chloroformate under strongly acidic conditions the protection, the sodium carbonate is used to carry out closed-loop reaction, the reaction is stable, is greatly improved yield, total yield of 48% the advantages.

SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF

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Total synthesis of a macrocyclic antibiotic, micrococcin P

The first total synthesis of a macrocyclic antibiotic, micrococcin P (1), was accomplished. After constructing the central 2,3,6-tristhiazolyl- substituted pyridine skeleton [Fragment A-C segment] (21) from ethyl 2-(2- bromoacetyl-6-dimethoxymethyl-3-pyridyl)thiazole-4-carboxylate (15) in 11 steps, successive fragment condensations of 21 with ethyl 2[(Z)-1-(O-t- butyldiphenylsilyl-L-threonylamino)-1-propenyl]thiazole-4-carboxylate (29) and (S)-1-(O-methoxymethyl-L-threonylamino)-2-(O-methoxymethyl)-2-propanol (25) [the protected Fragments B and D moieties, respectively] gave the protected Fragment A-B-C-D segment 34. Subsequent deprotection of all the protecting groups of 34 with trifluoroacetic acid and then cyclization by using BOP as condensing agent under high dilution conditions gave the expected micrococcin P (1). The synthetic 1 was identical with the natural 1 with respect to the chemical and physical properties.

Useful synthesis of 2,3,6-polythiazolesubstituted pyridine skeleton [Fragment A-C] of peptide antibiotic, micrococcin P

Practical synthesis of 2,3,6-trithiazolesubstituted pyridine skeleton [Fragment A-C] of peptide antibiotic micrococcin P was achieved from 3-cyano-6-dimethoxymethyl-2-pyridone in twelve steps.

Monobactams. Stereospecific Synthesis of (S)-3-Amino-2-oxoazetidine-1-sulfonic Acids

A facile, stereospecific synthesis of 3-amino-2-oxoazetidine-1-sulfonic acids (monobactams) by the cyclization of acyl sulfamates derived from β-hydroxy amino acids is described.