281573
(S)-(−)-1-Amino-2-(methoxymethyl)pyrrolidine
95%
Synonym(s):
SAMP
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About This Item
Empirical Formula (Hill Notation):
C6H14N2O
CAS Number:
Molecular Weight:
130.19
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1523794
Assay:
95%
Form:
liquid
InChI
1S/C6H14N2O/c1-9-5-6-3-2-4-8(6)7/h6H,2-5,7H2,1H3/t6-/m0/s1
SMILES string
COC[C@@H]1CCCN1N
InChI key
BWSIKGOGLDNQBZ-LURJTMIESA-N
assay
95%
form
liquid
optical activity
[α]20/D −79°, neat
optical purity
ee: 97% (GLC)
bp
42 °C/1.8 mmHg (lit.)
density
0.97 g/mL at 25 °C (lit.)
functional group
ether
Application
(S)-(-)-1-Amino-2-(methoxymethyl)pyrrolidine may be used as a chiral auxiliary in the asymmetric synthesis of (S)-2-ethylhexanoic acid and (S)-2-n-propyl-4-pentenoic acid. It can undergo 1,4-addition to (E)-alkenyl-cyclohexyl sulfonates in the presence of zinc bromide to form β-hydrazino-cyclohexyl sulfonates.
Undergoes condensation reactions with carbonyl compounds to produce hydrazones which are useful synthons in highly enantioselective syntheses.
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
161.6 °F - closed cup
flash_point_c
72 °C - closed cup
ppe
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
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Synlett, 897-897 (1992)
Yuanxia Qin et al.
Journal of agricultural and food chemistry, 67(11), 3168-3178 (2019-02-26)
In this study we report a secretory protein that was purified from Serratia marcescens strain S3 isolated from soil from the tobacco rhizosphere. Subsequent mass spectrometry and annotation characterized the protein as secretory alkaline metalloprotease (SAMP). SAMP plays a crucial
Synthesis, 725-725 (1993)
Loris R Lopetuso et al.
Inflammatory bowel diseases, 23(3), 392-403 (2017-02-02)
A large body of evidence supports a central role of TLR5 and its natural ligand, flagellin, in Crohn's disease (CD), with the precise mechanism(s) still unresolved. We investigated the role of flagellin/TLR5 in SAMP1/YitFc (SAMP) mice, a spontaneous model of
Asymmetric synthesis and enantioselective teratogenicity of 2-n-propyl-4-pentenoic acid (4-en-VPA), an active metabolite of the anticonvulsant drug, valproic acid.
Hauck R-S and Nau H.
Toxicology Letters, 49(1), 41-48 (1989)
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