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445797

D-Serine methyl ester hydrochloride

Name: <SC>D</SC>-Serine methyl ester hydrochloride
Brand: ALDRICH

98%

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About This Item

Linear Formula:

HOCH₂CH(NH₂)CO₂CH₃·HCl

CAS Number:

5874-57-7

Molecular Weight:

155.58

UNSPSC Code:

12352209

eCl@ss:

32160406

PubChem Substance ID:

24868202

NACRES:

NA.22

MDL number:

MFCD00066121

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Properties

Quality Level

100

assay

98%

form

solid

optical activity

[α]20/D −4°, c = 4 in ethanol

reaction suitability

reaction type: solution phase peptide synthesis

mp

163-166 °C (lit.)

application(s)

peptide synthesis

SMILES string

Cl.COC(=O)[C@H](N)CO

InChI

1S/C4H9NO3.ClH/c1-8-4(7)3(5)2-6;/h3,6H,2,5H2,1H3;1H/t3-;/m1./s1

InChI key

NDBQJIBNNUJNHA-AENDTGMFSA-N

Description

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Theoretical evidence for pyramidalized bicyclic serine enolates in highly diastereoselective alkylations.

Carlos Aydillo et al.

Chemistry (Weinheim an der Bergstrasse, Germany), 13(17), 4840-4848 (2007-03-17)

A new chiral serine equivalent and its enantiomer have been synthesized from (S)- and (R)-N-Boc-serine methyl esters (Boc: tert-butyloxycarbonyl). The use of these compounds as chiral building blocks has been demonstrated in the synthesis of alpha-alkyl alpha-amino acids by diastereoselective

Contribution of the anomeric effect to the solution and crystal structure of [1S,2S,6S,7s]-1,6-diaza-4,9-dioxa-2,7-dimethoxycarbonylbicyclo[4.4.1]undecane, a condensation product of L-serine methyl ester with formaldehyde.

J Sélambarom et al.

Carbohydrate research, 330(1), 43-51 (2001-02-24)

The reaction of L-serine methyl ester hydrochloride (1) with paraformaldehyde (2) in dichloromethane in the presence of triethylamine afforded a novel compound: [lS,2S,6S,7S]-1,6-diaza-4,9-dioxa-2,7-dimethoxycarbonylbicyclo[4.4.1]undecane (4) as a 2:3 adduct of 1 with 2. 1H and 13C NMR spectroscopy were unable to

Aziridinium from N,N-dibenzyl serine methyl ester: synthesis of enantiomerically pure beta-amino and alpha,beta-diamino esters.

Cédric Couturier et al.

Organic letters, 8(10), 2183-2186 (2006-05-05)

[reaction: see text] Reaction of N,N-dibenzyl-O-methylsulfonyl serine methyl ester with a variety of heteronucleophiles (sodium azide, sodium phthalimide, amines, thiols) and carbanions (sodium malonate) gave, via an aziridinium intermediate, the corresponding beta-amino or alpha,beta-diamino ester in good to excellent yield.

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Global Trade Item Number

SKU	GTIN
445797-25G	04061832642208
445797-5G	04061832642215