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706574

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

Name: <I>N</I>-Boc-<I>cis</I>-4-hydroxy-<SC>D</SC>-proline
Brand: ALDRICH

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

UNSPSC Code:

12352005

eCl@ss:

32160406

PubChem Substance ID:

329762652

NACRES:

NA.22

MDL number:

MFCD02094407

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Properties

assay

97%

form

solid

optical activity

[α]22/D +50.0°, c = 1 in methanol

mp

146-151 °C

application(s)

peptide synthesis

functional group

carboxylic acid, hydroxyl

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

Description

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

GHS07

signalword

Warning

hcodes

H319

pcodes

P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number

MKBC8255

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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)

Global Trade Item Number

SKU	GTIN
706574-1G	04061826130827