93204-36-5

Basic information

• Product Name: N-CARBOBENZYLOXY-D-SERINE METHYL ESTER
• Synonyms: N-CARBOBENZYLOXY-D-SERINE METHYL ESTER;Z-D-SERINE METHYL ESTER;Z-D-SER-OME;N-Z-D-serine methyl ester;(R)-Methyl 2-(((benzyloxy)carbonyl)aMino)-3-hydroxypropanoate;Cbz-D-Ser-OMe;(R)-Z-2-amino-3-hydroxypropionic acid methyl ester;Z-D-serine methyl ester≥ 97% (HPLC)
• CAS NO: 93204-36-5
• Molecular Formula: C₁₂H₁₅NO₅
• Molecular Weight: 253.25
• Product Categories: Amino Acid Derivatives;Peptide Synthesis;Serine
• Mol File: 93204-36-5.mol
• Article Data: 16

Chemical Properties

• Melting Point: 41-43 °C(lit.)
• Boiling Point: 170 °C0.01 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.2499 (rough estimate)
• Vapor Pressure: 1.3E-08mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: Store at 0-5°C
• PKA: 10.49±0.46(Predicted)
• CAS DataBase Reference: N-CARBOBENZYLOXY-D-SERINE METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: N-CARBOBENZYLOXY-D-SERINE METHYL ESTER(93204-36-5)
• EPA Substance Registry System: N-CARBOBENZYLOXY-D-SERINE METHYL ESTER(93204-36-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 93204-36-5(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C12H15NO5/c1-17-11(15)10(7-14)13-12(16)18-8-9-5-3-2-4-6-9/h2-6,10,14H,7-8H2,1H3,(H,13,16)/t10-/m1/s1

Upstream product

• 155846-56-3 (2R)-2-amino-3-hydroxypropanoic acid hydrochloride 
• 501-53-1 benzyl chloroformate 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 2104-89-4 D-serine methyl ester 
• 67-56-1 methanol 
• 503071-00-9 [(2R,5R)-4-oxo-2-[(1S)-triisopropylsilanyloxyethyl]-[1,3]oxazinan-5-yl]carbamic acid benzyl ester 
• 6081-61-4 N-(benzyloxycarbonyl)-D-serine 
• 5874-57-7 R-(-)-serine methyl ester hydrochloride 

Downstream Products

• 219676-45-6 methyl (R)-2-<(benzyloxycarbonyl)amino>-3-<(dimethyl)(1,1,2-trimethylpropyl)silyloxy>propanoate 
• 93204-37-6 (2R)-2-(benzyloxycarbonylamino)-3-tert-butoxypropionic acid methyl ester 
• 133464-37-6 (4R)-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester 
• 1150635-61-2 N-benzyloxycarbonyl-3-hydroxy-4-methoxy-5-methyl-L-phenylalaninol 

Relevant articles and documents

HETEROCYCLIC COMPOUNDS FOR THE TREATMENT OF ABNORMAL CELLULAR PROLIFERATION

This invention is in the area of heterocyclic-based compounds for the treatment of disorders involving abnormal cellular proliferation, including but not limited to tumors and cancers.

GLUCOSYLCERAMIDE SYNTHASE INHIBITORS FOR THE TREATMENT OF DISEASES

Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions associated with the enzyme glucosylceramide synthase (GCS).

Lewis acid facilitated regioselective synthesis of τ-histidinoalanine

τ-Histidinoalanine, with an unusual cross-link between His and Ala, is the central component of theonellamides, a family of bioactive peptidic natural products. Previous syntheses of this residue were plagued with low regioselectivity in the alkylation step. Herein, we report two novel routes to τ-histidinoalanine, involving alkylation of Boc-His-OMe with a serine-derived β-lactone and β-bromoalanine, respectively, as the electrophiles. The use of Mg(OTf)2 as a catalyst was found to be essential to ensure high regioselectivity for the τ-isomer, presumably due to the formation of a six-membered ring chelation involving the π-nitrogen atom of histidine.