N-Boc-(2R,3R)-3-Amino-2-hydroxy-3-p-tolyl-propionic acid
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N-Boc-(2R,3R)-3-Amino-2-hydroxy-3-p-tolyl-propionic acid

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Category
BOC-Amino Acids
Catalog number
BAT-013880
CAS number
1217647-86-3
Molecular Formula
C15H21NO5
Molecular Weight
295.33
IUPAC Name
(2R,3R)-2-hydroxy-3-(4-methylphenyl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
Density
1.2±0.1 g/cm3
Boiling Point
484.0±45.0 °C at 760 mmHg
InChI
InChI=1S/C15H21NO5/c1-9-5-7-10(8-6-9)11(12(17)13(18)19)16-14(20)21-15(2,3)4/h5-8,11-12,17H,1-4H3,(H,16,20)(H,18,19)/t11-,12-/m1/s1
InChI Key
DROMKHRRVLLBPM-VXGBXAGGSA-N
Canonical SMILES
CC1=CC=C(C=C1)C(C(C(=O)O)O)NC(=O)OC(C)(C)C
1. A short enantioselective synthesis of N-Boc-(2R,3R)-3-methyl-3-hydroxypipecolic acid from geraniol
Mark C Noe, Joel M Hawkins, Sheri L Snow, Lilli Wolf-Gouveia J Org Chem. 2008 Apr 18;73(8):3295-8. doi: 10.1021/jo800080t. Epub 2008 Mar 14.
The asymmetric synthesis of (2R,3R)-3-methyl-3-hydroxypipecolic acid, a key intermediate in the synthesis of dual MMP-13/aggrecanase inhibitors, is described. The title compound is prepared in seven steps with an overall yield of 41% starting from geraniol. Key steps in the synthesis include Sharpless asymmetric epoxidation, which establishes the chiral centers, and a one-pot oxidative olefin cleavage/reductive amination sequence that closes the piperidine ring.
2. Convergent synthesis of (2R,3R,8R,9R)-N-Boc-ADDA
Sebastien Meiries, Rodolfo Marquez J Org Chem. 2008 Jul 4;73(13):5015-21. doi: 10.1021/jo800574g. Epub 2008 Jun 11.
The convergent synthesis of N-Boc-(2R,3R,8R,9R,4E,6E)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldecadenoic acid (enantio-N-Boc-ADDA) is reported. Our flexible approach takes advantage of highly efficient non-aldol aldol and cross-metathesis methodologies.
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