Skip to Content
Merck
All Photos(1)

Documents

706574

Sigma-Aldrich

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

97%

Synonym(s):

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

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C10H17NO5
CAS Number:
Molecular Weight:
231.25
MDL number:
UNSPSC Code:
12352005
eCl@ss:
32160406
PubChem Substance ID:
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

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service