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
• Article Data: 49

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

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

Downstream Products

• 108149-60-6 methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate 
• 95715-86-9 (S)-2,2-dimethyl-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester 
• 721927-59-9 tert-butyl [(2R)-1-hydroxy-3-methoxypropan-2-yl]carbamate 
• 205647-74-1 (R)-tert-butyl 2,2-dimethyl-4-[(tosyloxy)methyl]-oxazolidine-3-carboxylate 
• 469886-48-4 (2S)-[1-(tert-butyldiphenylsilanyloxymethyl)-2-hydroxyethyl]carbamic acid tert-butyl ester 
• 126587-40-4 [(3S,4R)-6-Oxo-4-(phenyl-phenylsulfanyl-methyl)-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester 
• 126587-47-1 (4R,5S)-5<<(1,1-Dimethylethoxy)carbonyl>amino>-4-benzyltetrahydro-2H-pyran-2-one 
• 108149-64-0 (S)-(-)-α-methoxy-α-(trifluoromethyl)phenylacetic acid (4R)-2,2-dimethyl-3-[(1,1-dimethylethoxy)carbonyl]-4-hydroxymethyloxazolidine ester 
• 158584-96-4 (4R,5R)-5-(3-Benzyloxycarbonylamino-propyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 171564-50-4 (4R,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(3-methanesulfonyloxy-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 158584-95-3 (4R,5R)-5-(3-Azido-propyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 171564-51-5 (4R,5R)-5-(3-Benzyloxycarbonylamino-propyl)-4-methanesulfonyloxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 158584-94-2 (4R,5R)-3-N-tert-butoxycarbonyl-4-tert-butyldiphenylsilyloxymethyl-5-<3''-hydroxypropyl>-2,2-dimethyl-1,3-oxazolidine 
• 171564-49-1 (4R,5R)-5-Allyl-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 

Relevant articles and documents

APPLICATION OF MONOCYCLIC BETA-LACTAM COMPOUND IN PHARMACY

An application of a compound represented by formula (I) and pharmaceutically acceptable salts thereof in preparation of a drug for treating pneumonia.

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.

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.