95715-85-8

Basic information

• Product Name: BOC-D-SER-OME
• Synonyms: N-(TERT-BUTOXYCARBONYL)-D-SERINE METHYL ESTER;BOC-D-SERINE METHYL ESTER;BOC-D-SER-OME;D-Serine, N-[(1,1-dimethylethoxy)carbonyl]-, methyl ester (9CI);N-(TERT-BBUTOXYCARBONYL)-L-SERINE METHYL ESTER;BOC-D-SERINE METHYLESTER OIL;N-BOC-D-serine methylester;N-BOC-D-ser-methylester
• CAS NO: 95715-85-8
• Molecular Formula: C₉H₁₇NO₅
• Molecular Weight: 219.23
• EINECS: 1533716-785-6
• Product Categories: N-BOC;Heterocyclic Compounds;Serine [Ser, S];Amino Acid Derivatives;Peptide Synthesis;Serine;Amino Acids & Derivatives;Chiral Reagents;Intermediates;Pyridines
• Mol File: 95715-85-8.mol

Chemical Properties

• Boiling Point: 215 °C(lit.)
• Flash Point: >230 °F
• Appearance: Colorless to yellow/Liquid
• Density: 1.08 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.94E-06mmHg at 25°C
• Refractive Index: n20/D 1.453(lit.)
• Storage Temp.: Store at 0-5°C
• Solubility: Chloroform, Methanol
• PKA: 10.70±0.46(Predicted)
• CAS DataBase Reference: BOC-D-SER-OME(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-D-SER-OME(95715-85-8)
• EPA Substance Registry System: BOC-D-SER-OME(95715-85-8)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 95715-85-8(Hazardous Substances Data)

Usage

Chemical Properties

colorless to light yellow liquid

Uses

Protected D-Serine.

InChI:InChI=1/C9H17NO5/c1-9(2,3)15-8(13)10-6(5-11)7(12)14-4/h6,11H,5H2,1-4H3,(H,10,13)/t6-/m1/s1

Upstream product

• 186581-53-3 diazomethane 
• 3262-72-4 (R)-N-tert-butoxycarbonyl serine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 2104-89-4 D-serine methyl ester 
• 5874-57-7 R-(-)-serine methyl ester hydrochloride 
• 67-56-1 methanol 
• 312-84-5 D-Serine 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 2788-84-3 (S)-serine methyl ester 
• 74-88-4 methyl iodide 

Downstream Products

• 126645-21-4 methyl N-(tert-butoxycarbonyl)-O-[(4-methylphenyl)sulfonyl]-D-serinate 
• 301671-17-0 methyl (R)-3-azido-2-[(tert-butyloxycarbonyl)amino]propionate 
• 112418-19-6 (R)-2-N-tert-butoxycarbonylamino-3-(tert-butyldimethylsilyloxy)propionic acid methyl ester 
• 102507-13-1 N-(tert-butoxycarbonyl)-3-hydroxy-L-valine 
• 699005-66-8 (2R)-2-[N-(tert-butyloxycarbonyl)amino]-1-hydroxy-pentan-3-one 
• 699005-67-9 (2R)-2-[N-(tert-butyloxycarbonyl)amino]-3-hydroxy-1-phenyl-propan-1-one 
• 108149-60-6 methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate 
• 95715-87-0 (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine 
• 609812-03-5 tert-butyl (3E,1R,2S)-N-[2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-carbamate 
• 660852-86-8 (4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid 
• 896746-83-1 (R)-4-(2-benzoyl-phenylcarbamoyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 79069-15-1 N-(tert-butyloxycarbonyl)-O-benzyl-L-serinol 
• 108149-63-9 tert-butyl (4S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 469886-48-4 (2S)-[1-(tert-butyldiphenylsilanyloxymethyl)-2-hydroxyethyl]carbamic acid tert-butyl ester 

Relevant articles and documents

APPLICATION OF MONOCYCLIC BETA-LACTAM COMPOUND IN PHARMACY

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In search of small molecules that selectively inhibit mboat4

Ghrelin is a 28-residue peptide hormone produced by stomach P/D1 cells located in oxyntic glands of the fundus mucosa. Post-translational octanoylation of its Ser-3 residue, catalyzed by MBOAT4 (aka ghrelin O-acyl transferase (GOAT)), is essential for the binding of the hormone to its receptor in target tissues. Physiological roles of acyl ghrelin include the regulation of food intake, growth hormone secretion from the pituitary, and inhibition of insulin secretion from the pancreas. Here, we describe a medicinal chemistry campaign that led to the identification of small lipopeptidomimetics that inhibit GOAT in vitro. These molecules compete directly for substrate binding. We further describe the synthesis of heterocyclic inhibitors that compete at the acyl coenzyme A binding site.

Radical-Mediated Acyl Thiol-Ene Reaction for Rapid Synthesis of Biomolecular Thioester Derivatives

The thiol-ene ‘click’ reaction has emerged as a versatile process for carbon–sulfur bond formation with widespread applications in chemical biology, medicinal chemistry and materials science. Thioesters are key intermediates in a wide range of synthetic and biological processes and efficient methods for their synthesis are of considerable interest. Herein, we report the first examples of acyl-thiol-ene (ATE) for the synthesis of biomolecular thioesters, including peptide, lipid and carbohydrate derivatives. A key finding is the profound effect of the amino acid side chain on the outcome of the ATE reaction. Furthermore, radical generated thioesters underwent efficient S-to-N acyl transfer and desulfurisation to furnish ‘sulfur-free’ ligation products in an overall amidation process with diverse applications for chemical ligation and bioconjugation.

Chiral combinatorial preparation and biological evaluation of unique ceramides for inhibition of sphingomyelin synthase

Enantiomers or diastereomers of chiral bioactive compounds often exhibit different biological and toxicological properties. Here, we report the efficient synthesis of four stereoisomers of sphingosine and derivatization of unique chiral ceramides through a combinatorial chemistry by solid-phase activated resin ester. In addition, to test the effectivity of stereochemistry of ceramide, we demonstrated a cell-based assay of sphingomyelin synthase inhibition in the presence ofchiral unique ceramides, which suggested that libraries of this sort will be a rich source of biologically active synthetic molecules.

A Novel Agonist of the Type 1 Lysophosphatidic Acid Receptor (LPA1), UCM-05194, Shows Efficacy in Neuropathic Pain Amelioration

Neuropathic pain (NP) is a complex chronic pain state with a prevalence of almost 10% in the general population. Pharmacological options for NP are limited and weakly effective, so there is a need to develop more efficacious NP attenuating drugs. Activation of the type 1 lysophosphatidic acid (LPA1) receptor is a crucial factor in the initiation of NP. Hence, it is conceivable that a functional antagonism strategy could lead to NP mitigation. Here we describe a new series of LPA1 agonists among which derivative (S)-17 (UCM-05194) stands out as the most potent and selective LPA1 receptor agonist described so far (Emax = 118%, EC50 = 0.24 μM, KD = 19.6 nM; inactive at autotaxin and LPA2-6 receptors). This compound induces characteristic LPA1-mediated cellular effects and prompts the internalization of the receptor leading to its functional inactivation in primary sensory neurons and to an efficacious attenuation of the pain perception in an in vivo model of NP.

Method for preparing high-purity (R)-4-formyl-2,2-dimethyl-3-oxazoline tert-butyl carboxylate

The invention discloses a method for preparing high-purity (R)-4-formyl-2,2-dimethyl-3-oxazoline tert-butyl carboxylate. The method comprises the following steps: carrying out a reaction on D-serine and thionyl chloride in methanol to obtain a compound 2; carrying out a reaction on the compound 2 and Boc anhydride under triethylamine to obtain a compound 3; carrying out a reaction on the compound3 and 2,2-dimethoxypropane under the action of boron trifluoride diethyl ether to obtain a compound 4; and reducing the compound 4 and DIBAL-H are at a temperature of -60 DEG C to -80 DEG C to obtaina crude product, carrying out a reaction on the crude product and sodium sulfite to form salt, and purifying to obtain the high-purity (R)-4-formyl-2,2-dimethyl-3-oxazoline tert-butyl carboxylate. According to the invention, the salt forming is performed by using the properties of sodium sulfite and an aldehyde group, so that the purity of the salified product can reach 98%, the industrial standard is met, and the production operation is well facilitated.

MONOCYCLIC B-LACTAM COMPOUND FOR TREATING BACTERIAL INFECTION

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Generating Stereodiversity: Diastereoselective Fluorination and Highly Diastereoselective Epimerization of α-Amino Acid Building Blocks

Diastereoselective fluorination of N-Boc (R)- and (S)-2,2-dimethyl-4-((arylsulfonyl)methyl)oxazolidines and a previously unknown diastereoselective epimerization at the fluorine-bearing carbon atom α to the sulfone was realized. Diastereoselectivities of both reactions were excellent for benzothiazolyl sulfones, allowing access to two enantiomerically pure diastereomers from one chiral precursor. To demonstrate synthetic utility, the benzothiazolyl sulfones were converted to diastereomerically pure (S,S)- and (R,S)-benzyl sulfones via sulfinate salts and to amino acids. To understand the diastereoselectivities, DFT analysis was performed.