6368-20-3

Basic information

• Product Name: Boc-D-Serine
• Synonyms: BOC-D-SERINE H2O;BOC-D-SER-OH;BOC-D-SERINE;N-(TERT-BUTOXYCARBONYL)-D-SERIN;N-(TERT-BUTOXYCARBONYL)-D-SERINE;N-T-BOC-D-SERINE;N-ALPHA-T-BUTOXYCARBONYL-D-SERINE;N-ALPHA-TERT-BUTYLOXYCARBONYL-D-SERINE
• CAS NO: 6368-20-3
• Molecular Formula: C₈H₁₅NO₅
• Molecular Weight: 205.21
• EINECS: 444-670-6
• Product Categories: N-BOC;AMINOACIDS DERIVATIVES;Amino Acids;Boc-Amino Acids and Derivative;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;Boc-Amino acid series
• Mol File: 6368-20-3.mol
• Article Data: 50

Chemical Properties

• Melting Point: 91-95 °C(lit.)
• Boiling Point: 343.88°C (rough estimate)
• Flash Point: 186.7 °C
• Appearance: White powder
• Density: 1.2977 (rough estimate)
• Vapor Pressure: 1.61E-07mmHg at 25°C
• Refractive Index: 1.4540 (estimate)
• Storage Temp.: Store at RT.
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.62±0.10(Predicted)
• Water Solubility: almost transparency
• BRN: 1874714
• CAS DataBase Reference: Boc-D-Serine(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-D-Serine(6368-20-3)
• EPA Substance Registry System: Boc-D-Serine(6368-20-3)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 6368-20-3(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

Boc-D-serine is D-serine (S270975) with amine protected from eletrophiles by tert-butyloxycarbonyl group in organic synthesis. Boc-D-serine can be used to synthesize acetamido-methoxypropionamides such as Desacetyl Desmethyl Lacosamide (D288325) which is a potent anticonvulsant.

InChI:InChI=1/C8H15NO5/c1-8(2,3)14-7(13)9-5(4-10)6(11)12/h5,10H,4H2,1-3H3,(H,9,13)(H,11,12)/p-1/t5-/m1/s1

Upstream product

• 312-84-5 D-Serine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 155846-56-3 (2R)-2-amino-3-hydroxypropanoic acid hydrochloride 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 

Downstream Products

• 98541-64-1 N-(tert-butyloxycarbonyl)-D-serine β-lactone 
• 190586-78-8 N-tert-butoxycarbonyl-D-seryl-L-glutamic acid 1-methylamide 5-benzyl ester 
• 190586-80-2 N-tert-butoxycarbonyl-D-seryl-D-glutamic acid 1-methylamide 5-benzyl ester 
• 872413-85-9 N-tert-butoxycarbonylamino-O-thien-2-ylmethyl-D-serine 
• 616882-05-4 N-tert-butoxycarbonylamino-O-(2-methylbenzyl)-D-serine 
• 616881-87-9 N-tert-butoxycarbonylamino-O-(3-fluorobenzyl)-D-serine 
• 220534-06-5 N-tert-butoxycarbonylamino-O-(4-fluorobenzyl)-D-serine 
• 616882-07-6 N-tert-butoxycarbonylamino-O-(4-cyanobenzyl)-D-serine 
• 616881-99-3 N-tert-butoxycarbonylamino-O-(2,6-dichlorobenzyl)-D-serine 
• 616882-01-0 N-tert-butoxycarbonylamino-O-(4-chloro-2-fluorobenzyl)-D-serine 
• 616881-97-1 N-tert-butoxycarbonylamino-O-(2,3-dichlorobenzyl)-D-serine 
• 616882-09-8 N-tert-butoxycarbonylamino-O-(4-trifluoromethylbenzyl)-D-serine 
• 108998-79-4 (2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(S)-1-hydroxy-2-((S)-2-hydroxy-1,2,2-triphenyl-ethoxycarbonyl)-ethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 108998-79-4 (2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-1-hydroxy-2-((S)-2-hydroxy-1,2,2-triphenyl-ethoxycarbonyl)-ethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

?-LACTAMASE INHIBITOR AND USE THEREOF

Provided are a β-lactamase inhibitor of formula (I), or an ester, a stereoisomer or a pharmaceutically acceptable salt thereof, and a method of preparing the same. Further provided is a pharmaceutical composition comprising the β-lactamase inhibitor of formula (I), or the ester, the stereoisomer or pharmaceutically acceptable salt thereof. In addition, the present invention relates to a method for treating diseases caused by bacterial infection, which comprises administering the β-lactamase inhibitor of formula (I), or the ester, the stereoisomer or the pharmaceutically acceptable salt thereof to a patient or a subject in need.

In Silico Design and Enantioselective Synthesis of Functionalized Monocyclic 3-Amino-1-carboxymethyl-β-lactams as Inhibitors of Penicillin-Binding Proteins of Resistant Bacteria

As a complement to the renowned bicyclic β-lactam antibiotics, monocyclic analogues provide a breath of fresh air in the battle against resistant bacteria. In that framework, the present study discloses the in silico design and unprecedented ten-step synthesis of eleven nocardicin-like enantiomerically pure 2-{3-[2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-2-oxoazetidin-1-yl}acetic acids starting from serine as a readily accessible precursor. The capability of this novel class of monocyclic 3-amino-β-lactams to inhibit penicillin-binding proteins (PBPs) of various (resistant) bacteria was assessed, revealing the potential of α-benzylidenecarboxylates as interesting leads in the pursuit of novel PBP inhibitors. No deactivation by representative enzymes belonging to the four β-lactamase classes was observed, while weak inhibition of class C β-lactamase P99 was demonstrated.

AN IMPROVED PROCESS FOR THE PREPARATION OF LACOSAMIDE

The present invention relates to an improved process for the synthesis of (R)- Lacosamide in which free base of O-methyl-N-benzyl-D-Serinamide is not isolated before acylation. The process avoids the use of column chromatography and chiral resolution for the preparation of different stages of Lacosamide.