Sulfuric Acid → HCID 21968896, compound

HRID 1420481Notes

Reaction equation

HRID 1420481 reaction equation
C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O.[CH2:22]([O:29][C@H:30]1[C@H:35]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C@H:34]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C@H:33]([CH3:52])[O:32][C@@H:31]1[O:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][OH:64])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(Cl)Cl.S(=O)(=O)(O)O>C(O)C>[CH2:22]([O:29][C@H:30]1[C@H:35]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C@H:34]([O:44][CH2:45][C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[C@H:33]([CH3:52])[O:32][C@@H:31]1[O:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH:63]=[O:64])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 2724130Cornforth reagent2×HCID 21968897HCID 21968897, compound2×

Product 1

HCID 21968896HCID 21968896, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

PDC oxidation of 10-(2,3,4-tri-O-benzyl-β-L-fucopyranosyloxy)-n-decanol. Under an atmosphere of nitrogen, pyridinium dichromate (550 mg, 1.424 mmol) was added to a dry methylene chloride solution (20 mL) of 10-(2,3,4-tri-O-benzyl-β-L-fucopyranosyloxy)-n-decanol (580 mg, 0.982 mmol). The resulting brown slurry was stirred at room temperature under nitrogen. TLC analysis (visualization by UV and char with 10% sulfuric acid in ethanol) of the reaction mixture indicated complete consumption of the starting material and the formation of a new compound after 18 h. The reaction mixture was treated with ether (10 mL), filtered through silica gel and Celite with an ether wash (25 mL) and concentrated to an off-white oil. Chromatographic purification (silica gel, 20% ethyl acetate in hexanes) afforded 410 mg (0.697 mmol, 71%) of 10-(2,3,4-tri-O-benzyl-β-L-fucopyranosyloxy)-n-decanal as a clear oil. Rf =0.50 (silica gel, 30% ethyl acetate in hexanes); 1H NMR (CDCl3, 300 MHz) δ: 9.76 (t, J=1.8 Hz, 1H), 7.35 (m, 15H), 5.02 (d, J=8.1 Hz, 1H), 4.98 (d, J=7.2 Hz, 1H), 4.81 (m, 2H), 4.76 (d, J=5.7 Hz, 1H), 4.72 (d, J=5.7 Hz, 1H); 3.34 (d, J=7.8 Hz, 1H), 3.97 (dt, J=9.6, 6.0 Hz, 2H), 3.84 (dd, J=9.6, 7.8 Hz, 1H), 3.65-3.40 (m, 3H), 2.41 (dt, J=7.2, 1.5 Hz, 2H), 1.65 9m, 4H), 1.31 (s, 10H), 1.21 (d, J=6.3 Hz, 3H); MS (FAB+): 611.2 ((M+Na)+, 8), 595.2 ((M+Li)+, 100), 567.2 (12), 505.2 (10), 441.1 (7), 401.1 (6).

Workup

  1. customconsumption of the starting material
  2. additionThe reaction mixture was treated with ether (10 mL)
  3. filtrationfiltered through silica gel and Celite with an ether
  4. washwash (25 mL)
  5. concentrationconcentrated to an off-white oil
  6. customChromatographic purification (silica gel, 20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-a53a55e9e46b46f99c5ecaea0d2cc900
Source dataset
uspto-grants-2000_06
Patent number
US06071532

Reaction notes

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