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Chemical Structure| 1631070-69-3 Chemical Structure| 1631070-69-3

Structure of 1631070-69-3

Chemical Structure| 1631070-69-3

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Product Details of [ 1631070-69-3 ]

CAS No. :1631070-69-3
Formula : C9H17NO4
M.W : 203.24
SMILES Code : O=C(OC(C)(C)C)N[C@@H]1COC[C@@H]1O
English Name :tert-Butyl ((3R,4R)-rel-4-hydroxytetrahydrofuran-3-yl)carbamate
MDL No. :MFCD28166316

Safety of [ 1631070-69-3 ]

Application In Synthesis of [ 1631070-69-3 ]

* 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 [ 1631070-69-3 ]

[ 1631070-69-3 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 1631070-69-3 ]
  • [ 214629-29-5 ]
YieldReaction ConditionsOperation in experiment
50% With hydrogenchloride In methanol; water at 20℃; for 24h; 1 4.7.1
Synthesis of (3S,4S)-3-amino-4-hydroxytetrahydrofuran, (3S,4S)-(-)-18
General procedure: The optically pure product (-)-cis-7 or (-)-trans-7 (10 mg, 0.05 mmol) obtained from the CAL-B catalyzed hydrolysis, was dissolved in MeOH (1 mL) and treated with aq 3N HCl (20 μL). The mixture was stirred at room temperature for 24 h. Then, the solvent was removed under reduced pressure. The crude residue was purified by flash chromatography on silica gel (dichloromethane/methanol 8:2). The specific rotation signs of the pure products were in accordance with that reported for the (3S,4S)-(-)-3-amino-4-hydroxytetrahydrofuran and the (3R,4S)-(-)-3-amino-4-hydroxytetrahydrofuran. 4.7.2. (3S,4S)-()-18Yield 50%. [a]D25 6.0 (c 0.01, MeOH), ee >99%.
  • 2
  • [ CAS Unavailable ]
  • [ 103-80-0 ]
  • [ 1631070-58-0 ]
  • [ 1631070-69-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 12 h / 20 °C 2: immobilized Candida antarctica Lipase B; water / tert-butyl methyl ether / 10 h / 30 °C / Enzymatic reaction
  • 3
  • [ CAS Unavailable ]
  • [ 1631070-58-0 ]
  • [ 1631070-69-3 ]
YieldReaction ConditionsOperation in experiment
1: 49% 2: 48% With immobilized Candida antarctica Lipase B; water In tert-butyl methyl ether at 30℃; for 10h; Enzymatic reaction; enantioselective reaction; 2 4.4. General procedure for the enzymatic hydrolysis General procedure: The reaction mixture, containing the corresponding hydroxyacylated-N-Boc-aminoalcohol (15 mg), the lipase (15 mg) and H2O(10 equiv) in tBuOMe (2,5 mL), was shaken at 30 C and 250 rpmin an orbital shaker. The progress of the reaction was analyzedby TLC until the achievement of the required conversion (approximately).Then, the enzyme was removed by filtration and washedwith tBuOMe. The crude residue was purified by flash chromatographyon silica gel using a gradient hexane/EtOAc from 8:2 to 3:7.
  • 4
  • [ 24424-99-5 ]
  • [ 1631070-58-0 ]
  • [ 1631070-69-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trimethylphosphane; sodium hydroxide / tetrahydrofuran / 3 h / 20 °C 2: potassium carbonate / acetonitrile / 12 h / 20 °C 3: immobilized Candida antarctica Lipase B; water / tert-butyl methyl ether / 10 h / 30 °C / Enzymatic reaction
  • 5
  • [ 412278-24-1 ]
  • [ 1631070-69-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 16 h / 0 - 20 °C 2: lithium hydroxide monohydrate / methanol; water / 2 h / 20 °C
  • 6
  • [ 2923145-28-0 ]
  • [ 1631070-69-3 ]
YieldReaction ConditionsOperation in experiment
89% With lithium hydroxide monohydrate In methanol; water at 20℃; for 2h; 11.2 Step 2: Preparation of compound 11B Compound 11A (1.00 g, 2.84 mmol) was dissolved in methanol (10 mL) at room temperature, followed by addition of lithium hydroxide monohydrate (357 mg, 8.51 mmol) dissolved in water (2 mL), and stirred at room temperature for 2 hours. TLC (EA/PE = 3:7) showed that the raw material reaction was complete. Ethyl acetate and water were added to the reaction solution, and the liquid was separated. The organic phase was washed twice with a saturated sodium bicarbonate aqueous solution and then with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain compound 11B (512 mg, 89%). The crude product was directly subjected to the next step of reaction without purification.
 

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