57224-63-2

Basic information

• Product Name: N-Carbobenzyloxy-L-threonine methyl ester
• Synonyms: N-CARBOBENZOXY-L-THREONINE METHYL ESTER;N-CARBOBENZYLOXY-L-THREONINE METHYL ESTER;N-ALPHA-CARBOBENZOXY-L-THREONINE METHYL ESTER;Z-L-THREONINE METHYL ESTER;Z-THR-OME;Z-THREONINE-OME;L-Threonine, N-(phenylmethoxy)carbonyl-, methyl ester;CBZ-L-THREONINE METHYL ESTER
• CAS NO: 57224-63-2
• Molecular Formula: C₁₃H₁₇NO₅
• Molecular Weight: 267.28
• Mol File: 57224-63-2.mol

Chemical Properties

• Melting Point: 92-94 °C(lit.)
• Boiling Point: 410.46°C (rough estimate)
• Flash Point: 222.7 °C
• Appearance: White/Powder
• Density: 1.2100 (rough estimate)
• Vapor Pressure: 1.09E-08mmHg at 25°C
• Refractive Index: 1.4365
• Storage Temp.: -15°C
• PKA: 10.79±0.46(Predicted)
• Water Solubility: miscible
• BRN: 2220800
• CAS DataBase Reference: N-Carbobenzyloxy-L-threonine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-Carbobenzyloxy-L-threonine methyl ester(57224-63-2)
• EPA Substance Registry System: N-Carbobenzyloxy-L-threonine methyl ester(57224-63-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 57224-63-2(Hazardous Substances Data)

Usage

Chemical Properties

white to off-white powder

InChI:InChI=1/C13H17NO5/c1-9(15)11(12(16)18-2)14-13(17)19-8-10-6-4-3-5-7-10/h3-7,9,11,15H,8H2,1-2H3,(H,14,17)/t9-,11+/m1/s1

Upstream product

• 67-56-1 methanol 
• 5618-95-1 2-benzyloxycarbonylamino-3-hydroxy-butyric acid 
• 186581-53-3 diazomethane 
• 19728-63-3 N-benzyloxycarbonyl-L-treonine 
• 39994-75-7 L-threonine methyl ester hydrochloride 
• 501-53-1 benzyl chloroformate 
• 72-19-5 L-threonine 
• 245115-65-5 (2S)-(benzyloxycarbonylamino)-(3R)-(1,1-dimethylallyloxy)butyric acid methyl ester 
• 863650-79-7 C₁₆H₂₁NO₅ 
• 28130-04-3 Z-Thr-OEt 
• 74-88-4 methyl iodide 
• 39994-75-7 (+/-) threonine methyl ester hydrochloride 
• 39994-75-7 H-DL-aThr-OMe*HCl 
• 113479-92-8 2-Benzyloxycarbonylamino-4-oxo-pentanoic acid methyl ester 

Downstream Products

• 38229-27-5 (2-Hydroxy-1-methylcarbamoyl-propyl)-carbamic acid benzyl ester 
• 60027-55-6 (E)-α-<(Benzyloxycarbonyl)amino>crotonsaeure-methylester 
• 60027-61-4 methyl (2Z)-2-(N-benzyloxycarbonylamino)but-2-enoate 
• 38215-70-2 ((E)-1-Methylcarbamoyl-propenyl)-carbamic acid benzyl ester 
• 38215-67-7 (1-Methylcarbamoyl-2-nitrooxy-propyl)-carbamic acid benzyl ester 
• 49705-98-8 benzyl ((2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl)carbamate 
• 52785-41-8 N-benzyloxycarbonyl-O-tert-butylthreonine methyl ester 
• 77942-96-2 N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-L-threonine methyl ester 
• 74024-23-0 N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-threonine methyl ester 
• 77942-98-4 ester methylique de la N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-L-threonine 
• 77942-97-3 ester methylique de la N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-L-threonine 
• 135924-27-5 methyl 2-(benzyloxycarbonylamino)-2-(acetoxy)acetate 
• 102652-77-7 O-acetyl N-(benzyloxycarbonyl)-L-threoninehydroxamate 
• 68016-47-7 Z-Thr-Gly-NH2 

Relevant articles and documents

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The present invention relates to a synthesis method of Fmoc-O-tert-butyl-L-threoninol, and mainly solves the technical problems that in a process of Fmoc-thr(tbu)-oh reduction by sodium borohydride, the reaction temperature is strictly required and a FMoc protecting group is decomposed, resulting in low yield and high cost. The synthesis method of the invention comprises the following steps: a. L-threonine reacts with thionyl chloride to form L-threonine methyl ester hydrochloride; b. the L-threonine methyl ester hydrochloride under the action of sodium hydroxide is reacted with benzyl chloroformate to produce z-thr-ome; c. the Z-thr-ome reacts with introduced isobutene in the presence of methylene chloride and concentrated sulfuric acid, and alkali adjustment treatment is carried out to obtain z-thr (tbu)-ome; d. in the presence of acetone and water, the Z-thr(tbu)-ome is saponified with added alkali to obtain z-thr(tbu)-oh; e. the Z-thr(tbu)-oh is reduced to z-thr(tbu)-ol by sodium borohydride in tetrahydrofuran; f. the z-thr(tbu)-ol is hydrogenated in methanol to obtain H-thr(tbu)-ol; and g. N-(9-fluorenylmethoxycarbonyloxy)succinimide is added to the H-thr(tbu)-ol to obtain the Fmoc-O-tert-butyl -L-threoninol.

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