Ozone → HCID 15235476, compound

HRID 1456836Notes

Reaction equation

HRID 1456836 reaction equation
[O:1]=[O+][O-].[CH2:4]([O:11][C@@H:12]1[C@H:17]2[CH2:18][O:19][C@H:15]([O:16]2)[C@H:14]([CH:20]=C)[C@H:13]1[OH:22])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[BH4-].[Na+]>C(O)C.C(O)C.O>[CH2:4]([O:11][C@@H:12]1[C@H:17]2[CH2:18][O:19][C@H:15]([O:16]2)[C@H:14]([CH2:20][OH:1])[C@H:13]1[OH:22])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 24823OzoneHCID 4311764Sodium borohydride2×HCID 15119366HCID 15119366, compound

Product 1

HCID 15235476HCID 15235476, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 19096565Water ethanolSolvent

Procedure

A stream of ozone (0.36 mmol/min) was passed through a solution of 1,6-anhydro-4-O-benzyl-2-deoxy-2-C-vinyl-β-D-glucopyranose (8, 3.36 g, 12.8 mmol) in ethanol (100 ml) for 43.5 minutes. The solution of the ozonide was transferred to a three-necked round bottomed flask equipped with a thermometer and a dropping funnel containing a solution of NaBH4 (3.87 g, 102 mmol) in ethanol/water 1:1 (35 ml). The solution of NaBH4 was added dropwise in such a manner to keep the temperature below 20° C. (cooling on ice bath). After stirring for 45 min Amberlite IR 120, H+ (100 ml) was added. After stirring for another 30 minutes, the ion exchange resin was filtered off and rinsed with water. The solution was evaporated and co-concentrated with methanol (3×80 ml). The residue was a colorless syrup obtained in 96% (3.28 g) yield. This syrup was flash chromatographed using ethyl acetate/pentane 2:1 and ethyl acetate as eluent to give 9 in a 63% (2.14 g) yield as a crystalline compound. In some runs the crude syrup crystallized and was recrystallized from chloroform: mp. 111°-113°; [α]D20 =41.4° (c; 2.05, CH3OH). 13C-NMR (50 MHz, D2 O):δ139, 130.1, 129.8 (Ph); 102.0 (C-1);, 80.5 (C-4), 76.1 (C-3), 72.9 (OCH2Ph), 67.4 (C-5), 66.2 (C-6), 61.7 (C-2'), 49.0 ppm (C-2). Anal. Calc. for C14H18O5 : C, 63.15; H, 6.81. Found: C, 63.14; H, 6.79.

Workup

  1. customequipped with a thermometer and a dropping funnel
  2. temperaturethe temperature below 20° C. (cooling on ice bath)
  3. additionwas added
  4. filtrationthe ion exchange resin was filtered off
  5. washrinsed with water
  6. customThe solution was evaporated
  7. customobtained in 96% (3.28 g)
  8. customyield
  9. customchromatographed
  10. customto give 9 in a 63% (2.14 g)
  11. customyield as a crystalline compound
  12. customIn some runs the crude syrup crystallized
  13. customwas recrystallized from chloroform
  14. custom[α]D20 =41.4° (c; 2.05, CH3OH)

Sources & evidence

ORD record
ord-1a7f0df4cac44270a57fb1151a2284f8
Source dataset
uspto-grants-1998_12
Patent number
US05844102

Reaction notes

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