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Chemical Structure| 388578-39-0 Chemical Structure| 388578-39-0

Structure of 388578-39-0

Chemical Structure| 388578-39-0

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Product Details of [ 388578-39-0 ]

CAS No. :388578-39-0
Formula : C8H12O5
M.W : 188.18
SMILES Code : O[C@@H]1[C@@H](C#C)O[C@H](CO)[C@@H](O)[C@@H]1O

Safety of [ 388578-39-0 ]

Application In Synthesis of [ 388578-39-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 388578-39-0 ]

[ 388578-39-0 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 953410-86-1 ]
  • [ 388578-39-0 ]
  • (2R,3S,4R,5S,6R)-2-(hydroxymethyl)-6-[2-[7-[2-[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]ethynyl]-1H-indazol-5-yl]ethynyl]tetrahydropyran-3,4,5-triol [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% With copper(l) iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 80℃;Inert atmosphere; Preparation of Compound 212 (Method D) (2R,3S,4R,5S,6R)-2-(hydroxymethyl)-6-[2-[7-[2-[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6- (hydroxymethyl)tetrahydropyran-2-yl]ethynyl]-lH-indazol-5-yl]ethynyl]tetrahydropyran- -triol To a reaction tube charged with 5-bromo-7-iodo-lH-indazole (45.0 mg, 0.139 mmol) prepared following the procedure described in PCT Int. Appl, 2007117465, Pd(dppf)Cl2. CH2CI2 (6.0 mg, 0.0082 mmol) and Cul (6.0 mg, 0.032 mmol), capped and degassed (vacuum then nitrogen flush, 2x) is added Intermediate M (500 of 0.53 M, 0.265 mmol) as a solution in DMF and DIPEA (400 μ). The reaction tube is degassed again, transferred to a preheated (80C) oil bath and stirred overnight. After cooling down to RT, the reaction mixture is passed through a 200 mg Si-DMT cartridge, rinsed with portions of MeOH and purified by reverse phase HPLC. The fractions are combined and freeze-dried, providing the title compound (18.2 mg, 27% yield) as a fluffy white solid. XH NMR (400 MHz, CD30D) δ 8.14 (s, 1H), 7.97 (d, J = 1.3 Hz, 1H), 7.60 (d, J = 1.2 Hz, 1H), 5.01 (d, J = 2.1 Hz, 1H), 4.93 - 4.78 (m, 1H), 4.16 - 4.09 (m, 1H), 4.06 - 4.01 (m, 1H), 4.01 - 3.81 (m, 6H), 3.80 - 3.70 (m, 2H), 3.69 - 3.58 (m, 2H). ESI-MS m/z: 491.44 (M+l)+
  • 2
  • [ 953410-86-1 ]
  • [ 388578-39-0 ]
  • (2R,3S,4R,5S,6R)-2-[2-(5-bromo-1 H-indazol-7-yl)ethynyl]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol [ No CAS ]
YieldReaction ConditionsOperation in experiment
14% With copper(l) iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 - 50℃; for 48h;Inert atmosphere; Intermediate B3 (78 mg, 0.290 mmol), Cul (10 mg, 0.053 mmol) and Pd(dppf)C12.DCM (10 mg, 0.0 14 mmol) were loaded in a pressure vial, capped and degassed (vacuum then nitrogen flush, 3x). A solution of Intermediate Ml (500 jiL of 0.53 M, 0.265 mmol) in DMF was added, followed by DIPEA (0.4 mL). The vial was degassed again andtransferred to a preheated (80C) oil bath and stined overnight (20h). The crude reaction mixture was passed through a 200 mg Si-DMT cartridge, and rinsed with portions of DMSO to produce a 1 mL sample, which was purified by reverse phase HPLC. The fractions were combined and freeze-dried to provide the title compound (32 mg, 51% yield).; The title compound was prepared following the procedure used for Compound 15,using Intermediate B8 as starting material. The reaction mixture was stined at RT for 24 h thenat 50C for 24h. After purification by reverse-phase flash chromatography on a BiotageTM 30 gC18 silica cartridge using a gradient of MeCN in H20 (10 to 90%) as eluent and freeze-drying ofthe combined fractions, the title compound (47 mg, 14% yield) was obtained. ‘H NMR (400MHz, CD3OD) ö 8.08 (s, 1H), 8.00 (s, 1H), 7.63 (s, 1H), 5.01 (d, J = 2.1 Hz, 1H), 4.14 - 4.09 (m,1H), 3.97 (dd, J = 9.4, 3.3 Hz, 1H), 3.93 (dd, J = 11.5, 2.1 Hz, 1H), 3.91 - 3.85 (m, 1H), 3.75(dd, J = 11.5, 6.2 Hz, 1H), 3.64 (t, J = 9.5 Hz, 1H). ESI-MS mlz calc. 382.0 1645, found 383.26(M+1).
  • 3
  • [ 953410-86-1 ]
  • [ 108-24-7 ]
  • [ 388578-39-0 ]
  • (2R,3S,4R,5S,6R)-2-[2-(5-bromo-1 H-indazol-7-yl)ethynyl]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% In a pressure vessel charged with Intermediate B8 (2.33 g, 7.22 mmol), Cul (273 mg,1.43 mmol) and Pd(dppf)C12.DCM (266 mg, 0.364 mmol), capped and degassed (placed under vacuum and flushed with N2, 3x) was added Intermediate Ml (15 mL of 0.53 M, 7.95 mmol) solution in DMF followed by DIPEA (12 mL). The pressure vessel was degassed again, sealed and transfened to a preheated (50C) oil bath and stined overnight. After cooling down to RT,pyridine (15 mL, 186 mmol) was added, followed by acetic anhydride (15 mL, 159 mmol) and the resulting mixture was stirred overnight, then passed through a silica pad and rinsed with 200 mL EtOAc. The filtrate was transfened to a separatory funnel and washed with H20 (2 x 100 mL) and aqueous saturated NH4C1 solution (2 x 100 mL), dried over Na2SO4, filtered and concentrated, then co-evaporated with heptane (2x). The crude residue was purified by flashchromatography on a BiotageTM snap lOOg silica cartridge, using a gradient of EtOAc (10-60%) in Hex, as eluent. The fractions were combined and concentrated to provide the title compounds (as a mixture of regioisomers which were not separated) (3.03 g, 71% yield).; [000198] To a stined suspension of the regioisomers from Step 1(3.00 g, 5.06 mmol) in MeOH(20 mL) was added a solution of NaOMe (20.0 mL of 0.5 M, 10.1 mmol) in MeOH. Afterstifling for 30 mm, the reaction mixture was diluted with MeOH (25 mL) and treated with a minimal amount of prewashed Dowex 50WX4-400 resin (until pH is slightly acidic), diluted with THF (20 mL), filtered and washed with portions of MeOH/THF (1:1, 4x10 mL). The combined filtrates were concentrated to provide the title compound (1.85 g, 96% yield).
  • 4
  • [ 953410-86-1 ]
  • [ 108-24-7 ]
  • [ 388578-39-0 ]
  • [(2R,3R,4R,5R,6R)-3,4,5-triacetoxy-6-[2-(1-acetyl-5-bromo-indazol-7-yl)ethynyl]tetrahydropyran-2-yl]methyl acetate [ No CAS ]
  • (2R,3R,4R,5R, 6R)-2-(acetoxymethyl)-6-((2-acetyl-5-bromo-2H-indazol-7-yl)ethynyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In a pressure vessel charged with Intermediate B8 (2.33 g, 7.22 mmol), Cul (273 mg,1.43 mmol) and Pd(dppf)C12.DCM (266 mg, 0.364 mmol), capped and degassed (placed under vacuum and flushed with N2, 3x) was added Intermediate Ml (15 mL of 0.53 M, 7.95 mmol) solution in DMF followed by DIPEA (12 mL). The pressure vessel was degassed again, sealed and transfened to a preheated (50C) oil bath and stined overnight. After cooling down to RT,pyridine (15 mL, 186 mmol) was added, followed by acetic anhydride (15 mL, 159 mmol) and the resulting mixture was stirred overnight, then passed through a silica pad and rinsed with 200 mL EtOAc. The filtrate was transfened to a separatory funnel and washed with H20 (2 x 100 mL) and aqueous saturated NH4C1 solution (2 x 100 mL), dried over Na2SO4, filtered and concentrated, then co-evaporated with heptane (2x). The crude residue was purified by flashchromatography on a BiotageTM snap lOOg silica cartridge, using a gradient of EtOAc (10-60%) in Hex, as eluent. The fractions were combined and concentrated to provide the title compounds (as a mixture of regioisomers which were not separated) (3.03 g, 71% yield).
 

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