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706574

Sigma-Aldrich

N-Boc-cis-4-hydroxy-D-proline

97%

Synonym(s):

(2R,4R)-N-Boc-4-hydroxy-2-pyrrolidinecarboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C10H17NO5
CAS Number:
135042-12-5
Molecular Weight:
231.25
MDL number:
MFCD02094407
UNSPSC Code:
12352005
eCl@ss:
32160406
PubChem Substance ID:
329762652
NACRES:
NA.22

Assay

97%

form

solid

optical activity

[α]22/D +50.0°, c = 1 in methanol

mp

146-151 °C

application(s)

peptide synthesis

storage temp.

2-8°C

SMILES string

CC(C)(C)OC(=O)N1C[C@H](O)C[C@@H]1C(O)=O

InChI

1S/C10H17NO5/c1-10(2,3)16-9(15)11-5-6(12)4-7(11)8(13)14/h6-7,12H,4-5H2,1-3H3,(H,13,14)/t6-,7-/m1/s1

InChI key

BENKAPCDIOILGV-RNFRBKRXSA-N

Application

N-Boc-cis-4-hydroxy-D-proline can be used:
  • As a starting material in the synthesis of DNA mimicking pyrrolidine peptide nucleic acid (PNA) analog.
  • In the synthesis of biologically important macrocyclic dilactones.
  • As an intermediate in the synthesis of histamine H3 receptor antagonists.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Precautionary Statements

P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Synthesis of macrocyclic dilactones by cyclization of sulfonium salts
Nakamura T, et al.
The Journal of Organic Chemistry, 57(14), 3783-3789 (1992)
Novel substituted pyrrolidines are high affinity histamine H3 receptor antagonists
Stocking EM, et al.
Bioorganic & Medicinal Chemistry Letters, 20(9), 2755-2760 (2010)
Pyrrolidine PNA: A novel conformationally restricted PNA analogue
Puschl A, et al.
Organic Letters, 2(26), 4161-4163 (2000)

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