Boc-(3R)-1,2,3,4-tetrahydroisoquinoline-7-hydroxy-3-carboxylic acid
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Boc-(3R)-1,2,3,4-tetrahydroisoquinoline-7-hydroxy-3-carboxylic acid

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Boc-(3R)-1,2,3,4-tetrahydroisoquinoline-7-hydroxy-3-carboxylic acid is an intermediate used to prepare highly potent and selective opioid κ receptor antagonists.

Category
BOC-Amino Acids
Catalog number
BAT-007915
CAS number
214630-00-9
Molecular Formula
C15H19NO5
Molecular Weight
293.32
Boc-(3R)-1,2,3,4-tetrahydroisoquinoline-7-hydroxy-3-carboxylic acid
IUPAC Name
(3R)-7-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonyl]-3,4-dihydro-1H-isoquinoline-3-carboxylic acid
Synonyms
Boc-7-hydroxy-D-Tic-OH; Boc-D-Tic(OH)-OH; (R)-2-(tert-Butoxycarbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid; BOC-7-HYDROXY-D-TIC-OH; (R)-7-Hydroxy-2-Boc-3,4-dihydro-isoquinoline-3-carboxylic acid; Boc-D-Tic(7-OH)-OH; (3r)-2-(tert-butoxycarbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid; Boc-D-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid
Appearance
White to off-white powder
Purity
≥ 99% (HPLC)
Density
1.302±0.06 g/cm3 (Predicted)
Melting Point
196-202 °C
Boiling Point
496.7±45.0 °C (Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C15H19NO5/c1-15(2,3)21-14(20)16-8-10-6-11(17)5-4-9(10)7-12(16)13(18)19/h4-6,12,17H,7-8H2,1-3H3,(H,18,19)/t12-/m1/s1
InChI Key
ZJYIVHWYSNWCSX-GFCCVEGCSA-N
Canonical SMILES
CC(C)(C)OC(=O)N1CC2=C(CC1C(=O)O)C=CC(=C2)O
1. 3-Aminopyrrolidine-4-carboxylic acid as versatile handle for internal labeling of pyrrolidinyl PNA
Nisanath Reenabthue, Chalothorn Boonlua, Chotima Vilaivan, Tirayut Vilaivan, Chaturong Suparpprom Bioorg Med Chem Lett. 2011 Nov 1;21(21):6465-9. doi: 10.1016/j.bmcl.2011.08.079. Epub 2011 Aug 23.
Conformationally restricted pyrrolidinyl PNAs with an α/β-dipeptide backbone consisting of a nucleobase-modified proline and a cyclic five-membered amino acid spacer such as (1S,2S)-2-aminocyclopentanecarboxylic acid (ACPC) (acpcPNA) can form very stable hybrids with DNA with high Watson-Crick base pairing specificity. This work aims to explore the effect of incorporating 3-aminopyrrolidine-4-carboxylic acid (APC), which is isosteric to the ACPC spacer, into the acpcPNA. It is expected that the modification should not negatively affect the DNA binding properties, and that the additional nitrogen atom in the APC should provide a handle for internal modification. Orthogonally-protected (N(3)-Fmoc/N(1)-Boc and N(3)-Fmoc/N(1)-Tfa) APC monomers have been successfully synthesized and incorporated into the acpcPNA by Fmoc-solid-phase peptide synthesis. T(m), UV and CD spectroscopy confirmed that the (3R,4S)-APC could substitute the (1S,2S)-ACPC spacer in the acpcPNA with only slightly decreasing the stability of the hybrids formed between the modified acpc/apcPNA and DNA. In contrast, the (3S,4R) enantiomer of APC caused substantial destabilization of the hybrids. Furthermore, a successful on-solid-support internal labeling of the acpc/apcPNA via amide bond formation between pyrene-1-carboxylic acid or 4-(pyrene-1-yl) butyric acid and the pyrrolidine nitrogen atom of the APC spacer has been demonstrated. Fluorescence properties of the pyrene-labeled acpc/apcPNAs are sensitive to their hybridization states and can readily distinguish between complementary and single-mismatched DNA targets.
2. Synthesis of Enantiomerically Pure N-Boc-Protected 1,2,3-Triaminopropylphosphonates and 1,2-Diamino-3-Hydroxypropylphosphonates
Aleksandra Trocha, Dorota G Piotrowska, Iwona E Głowacka Molecules. 2019 Oct 25;24(21):3857. doi: 10.3390/molecules24213857.
All possible isomers of 1,2,3-tri(N-tert-butoxycarbonylamino)propylphosphonate 6 were synthesized from the respective diethyl [N-(1-phenylethyl)]-1-benzylamino-2,3-epiiminopropylphosphonates 5 via opening the aziridine ring with trimethylsilyl azide (TMSN3) followed by hydrogenolysis in the presence of di-tert-butyl dicarbonate (Boc2O). [N-(1-phenylethyl)]-1-benzylamino-2,3-epiiminopropylphosphonates (1R,2R,1'S)-5a and (1S,2S,1'R)-5c were smoothly transformed into diethyl 3-acetoxy-1-benzylamino-2-[N-(1-phenylethyl)amino]propylphosphonates (1R,2R,1'S)-9a and (1S,2S,1'R)-9c, respectively by the opening of the aziridine ring with acetic acid. Transformations of [N-(1-phenylethyl)]-1-benzylamino-2,3-epiiminopropylphosphonates (1S,2R,1'S)-5b and (1R,2S,1'R)-5d into diethyl 3-acetoxy-1-benzylamino-2-[(1-phenylethyl)amino]propylphosphonates (1S,2R,1'S)-9b and (1R,2S,1'R)-9d were accompanied by the formation of ethyl {1-(N-benzylacetamido)-3-hydroxy-2-[(1-phenylethyl)amino]propyl}phosphonate (1S,2R,1'S)-10b and (1R,2S,1'R)-10d and 3-(N-benzylacetamido)-4-[N-(1-phenylethyl)]amino-1,2-oxaphospholane (3S,4R,1'S)-11b and (3R,4S,1'R)-11d as side products. Diethyl (1R,2R)-, (1S,2S)-, (1S,2R)- and (1R,2S)-3-acetoxy-1,2-di(N-tert-butoxycarbonylamino)propylphosphonates 7a-7d were obtained from the respective 3-acetoxy-1-benzylamino-2-[N-(1-phenylethyl)amino]propylphosphonates 9a-9d by hydrogenolysis in the presence of Boc2O.
3. Synthesis of enantiopure trans-N-Boc-3-aminobicyclo[2.2.2]octane-2-carboxylic acids and their bicyclic 1,3-amino alcohol derivatives via the [4+2] cycloaddition of 1,3-cyclohexadiene to a chiral β-nitroacrylate
Monique Calmes, Françoise Escale, Claude Didierjean, Jean Martinez Chirality. 2011 Mar;23(3):245-9. doi: 10.1002/chir.20906. Epub 2010 Oct 6.
The chiral β-nitroacrylate 2 derived from the (R)- or (S)-4-(3-hydroxy-4,4-dimethyl-2-oxopyrrolidin-1-yl) benzoic acid 1 acts as a reactive dienophile in a diastereoselective Diels-Alder reaction with 1,3-cyclohexadiene. The major cycloadducts have been isolated and transformed into enantiopure trans(2S,3S)- or (2R,3R)-N-Boc-3-aminobicyclic[2,2,2]octane-2-carboxylic acids 5. The trans-(2S,3S)- or (2R,3R)-N-Boc 3-(hydoxymethyl)-2-aminobicyclic[2,2,2]octane 6 derivatives were also obtained.
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