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| | CarbaMicacid,N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-diMethyl-4H-cyclopenta-1,3-dioxol-4-yl]-,phenylMethyl ester Basic information |
| Product Name: | CarbaMicacid,N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-diMethyl-4H-cyclopenta-1,3-dioxol-4-yl]-,phenylMethyl ester | | Synonyms: | CarbaMicacid,N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-diMethyl-4H-cyclopenta-1,3-dioxol-4-yl]-,phenylMethyl ester;Benzyl((3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)carbamate-Tetrahydro-6-hydroxy-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]carbamic acid phenyl methyl ester;N-[(3aS,4R,6S,6aR)-Tetrahydro-6-hydroxy-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]carbamicacid phenylmethyl ester;N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-diMethyl-4H-cyclopenta-1,3-dioxol-4-yl]-,phenylMethyl ester;((3AS 4R 6S 6AR)6-HYDROXY-2,2-DIMETHYL-TETRAHYDROCYCLOPENTA(1,3)DIOXOL 4,YL)CARBAMIC ACID BENZYL ESTER;Benzyl((3aS, 4R, 6S, 6aR)-6-hydroxy-2,2-diMethyltetrahydro-3aH-cyclopenta[1,3]-dioxol-4yl)carbaMate;CarbaMic acid,N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-;benzyl N-[(3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]carbamate | | CAS: | 274693-53-7 | | MF: | C16H21NO5 | | MW: | 307.34 | | EINECS: | 700-846-7 | | Product Categories: | | | Mol File: | 274693-53-7.mol | ![CarbaMicacid,N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-diMethyl-4H-cyclopenta-1,3-dioxol-4-yl]-,phenylMethyl ester Structure](CAS/GIF/274693-53-7.gif) |
| | CarbaMicacid,N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-diMethyl-4H-cyclopenta-1,3-dioxol-4-yl]-,phenylMethyl ester Chemical Properties |
| Melting point | 117 - 119°C | | Boiling point | 489.1±45.0 °C(Predicted) | | density | 1.28 | | storage temp. | Inert atmosphere,Store in freezer, under -20°C | | solubility | Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly) | | form | Solid | | pka | 11.41±0.60(Predicted) | | color | White to Off-White | | InChI | InChI=1S/C16H21NO5/c1-16(2)21-13-11(8-12(18)14(13)22-16)17-15(19)20-9-10-6-4-3-5-7-10/h3-7,11-14,18H,8-9H2,1-2H3,(H,17,19)/t11-,12+,13+,14-/m1/s1 | | InChIKey | VPICQZQITAJOQA-ZOBORPQBSA-N | | SMILES | C(OCC1=CC=CC=C1)(=O)N[C@H]1[C@@]2([H])[C@@]([H])([C@@H](O)C1)OC(C)(C)O2 |
| | CarbaMicacid,N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-diMethyl-4H-cyclopenta-1,3-dioxol-4-yl]-,phenylMethyl ester Usage And Synthesis |
| Uses | Phenylmethyl ester N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]-Carbamic acid is a useful chiral building block. It has been used in the synthesis of all-cis carbocyclic precursor of ticagrelor via oxidation/stereoselective reduction sequences. | | Synthesis | Step 7: To a tetrahydrofuran:water mixture of (3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopentadieno[d][1,3]dioxol-4-ol (17.0 g, 98.15 mmol, 1.00 eq.) and sodium carbonate (20.8 g, 196.24 mmol, 2.00 eq.) at 0°C (5:1, 600 mL) mixed solution, benzyl chloroformate (18.4 g, 107.86 mmol, 1.05 eq.) was slowly added. After completion of the reaction, extraction was carried out with ethyl acetate (3×200 mL) and the organic phases were combined to give the title compound N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-dimethyl-4H-cyclopentaeno-1,3-dioxolan-4-yl]carbamic acid benzyl ester as a white solid (20.5 g, 68% yield) after standard post-processing. The product was characterized by 1H NMR (300 MHz, CDCl3), δ: 7.30-7.39 (m, 5H), 5.20 (s, 2H), 4.60 (d, J=5.4 Hz, 1H), 4.50 (d, J=5.4 Hz, 1H), 4.27 (s, 1H), 4.19 (d, J=5.7 Hz, 1H), 2.26 (m. 1H), 1.71 (d, J=14.4Hz, 1H), 1.47 (s, 3H), 1.28 (s, 3H). | | References | [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 21, p. 6013 - 6018
[2] Patent: WO2011/17108, 2011, A2. Location in patent: Page/Page column 38
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 11, p. 3598 - 3602
[4] Patent: WO2012/138981, 2012, A2. Location in patent: Page/Page column 38
[5] Patent: CN106279095, 2017, A. Location in patent: Paragraph 0023; 0046 |
| | CarbaMicacid,N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-diMethyl-4H-cyclopenta-1,3-dioxol-4-yl]-,phenylMethyl ester Preparation Products And Raw materials |
| Raw materials | Benzyl chloroformate-->(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol-->Water-->Sodium carbonate-->Tetrahydrofuran | | Preparation Products | Ethyl 2-(((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)acetate oxalate |
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