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Chemical Structure| 72-87-7 Chemical Structure| 72-87-7

Structure of 72-87-7

Chemical Structure| 72-87-7

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Product Details of [ 72-87-7 ]

CAS No. :72-87-7
Formula : C8H15NO6
M.W : 221.21
SMILES Code : O[C@H]1[C@H](O)[C@@H](CO)OC(O)[C@@H]1NC(C)=O
English Name :N-((3R,4R,5S,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide
MDL No. :MFCD00061615

Safety of [ 72-87-7 ]

Application In Synthesis of [ 72-87-7 ]

* 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 [ 72-87-7 ]

[ 72-87-7 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 72-87-7 ]
  • [ 4271-28-7 ]
YieldReaction ConditionsOperation in experiment
With sodium tetrahydroborate
  • 2
  • [ 72-87-7 ]
  • [ 487027-19-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridine / 0 °C 2: LiN3 / dimethylformamide / 40 °C 3: pyridine / 20 °C
Multi-step reaction with 3 steps 1: pyridine / 0 °C 2: pyridine 3: sodium azide / N,N-dimethyl-formamide / 80 °C
Multi-step reaction with 3 steps 1: pyridine / 18 h / -20 °C 2: sodium azide / N,N-dimethyl-formamide / 3 d / 50 °C 3: pyridine / 16 h / 20 °C
Multi-step reaction with 3 steps 1: pyridine / Cooling with ice 2: sodium azide / N,N-dimethyl-formamide / 60 °C 3: pyridine / 0 °C

  • 3
  • [ 72-87-7 ]
  • [ 14316-61-1 ]
  • [ 1536202-07-9 ]
YieldReaction ConditionsOperation in experiment
100% With pyridine; dmap; at 20℃; for 12h;Cooling with ice; An ice-cold solution of compound 97 (4.87 g, 22.0 mmol) in dry pyridine (70 mL) was treated with <strong>[14316-61-1]phenoxyacetic anhydride</strong> (37.8 g, 132.0 mmol) and 4- dimethylaminopyridine (26.9 mg, 220 ^mol). After stirring at r.t. for 12 h, the mixture was concentrated and co-evaporated with toluene in vacuo. The resultant was diluted by DCM (400 mL) and washed with sat. NaHC03 (1 x 400 mL). Upon extraction, the organic layer was separated, dried with a2S04, filtered and concentrated in vacuo. The resultant was subjected to column chromatography and was eluted with an EtOAc/hexane gradient to give pure compound 98 (16.7 g, 22.0 mmol, 100 % yield). 1H NMR (399 MHz, CDC13) delta 7.36 - 6.75 (m, 20H), 6.27 - 6.20 (d, 1H), 5.43 - 5.36 (m, 1H), 5.22 - 5.06 (m, 2H), 4.81 - 4.65 (m, 3H), 4.60 - 4.52 (m, 2H), 4.45 - 4.29 (m, 2H), 4.17 - 4.02 (m, 2H), 3.97 - 3.87 (m, 1H), 1.85 and 1.74 (d, 3H, rotamers); 13C MR (100 MHz, CDC13) delta 170.20, 168.78, 168.70, 168.36, 167.52, 157.56, 157.48, 157.40, 130.09, 129.70, 129.66, 129.60, 122.32, 122.01, 121.94, 114.61, 114.58, 114.58, 114.39, 91.93, 68.37, 68.25, 67.30, 64.54, 61.25, 46.43, 22.95; R/= 0.35 (1 : 1 EtOAc/hexane).
  • 4
  • [ 689-02-1 ]
  • [ 72-87-7 ]
  • [ 2630942-94-6 ]
  • [ 2630942-95-7 ]
YieldReaction ConditionsOperation in experiment
In methanol for 3h; Reflux; Overall yield = 65 percent; Synthesis of 3-thiopropionylhydrazoles of aldoses 3a-3d (general procedure) General procedure: A solution of 1.20 g (10 mmol) of compound 2 and 10 mmol of the corresponding monosaccharide in 30 mL of OH was refluxed during 3 h. The mixture was cooled down; white crystals were filtered off, dried in vacuum, and stored in a dessicator over P2O5.
 

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