Dimethyl Sulfoxide → HCID 86753402, compound

HRID 1456838Notes

Reaction equation

HRID 1456838 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:18][C@@H:19]1[C@@H:26]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C@H:25]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C@@H:24]([CH2:43][CH2:44][OH:45])[O:23][C@H:20]1[O:21][CH3:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl.C(Cl)(Cl)Cl.O>[CH2:11]([O:18][C@@H:19]1[C@@H:26]([O:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C@H:25]([O:35][CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C@@H:24]([CH2:43][CH:44]=[O:45])[O:23][C@H:20]1[O:21][CH3:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 67629587HCID 67629587, compound

Product 1

HCID 86753402HCID 86753402, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent4×

Conditions

Temperature
-78 °C

Procedure

A solution of oxalyl chloride (110 μl), 1.3 mmol) in dry dichloromethane (1.55 ml) was stirred under nitrogen atmosphere and cooled to -78° C. Dimethyl sulfoxide (0.178 ml, 2.5 mmol) in dichloromethane (0.67 ml) was added dropwise over 10 min. After stirring for 5 min methyl 2,3,4-tri-O-benzyl-6-deoxy-β-D-gluco-hepto-1,5-pyranoside (0.40 g, 0.8 mmol) dissolved in dichloromethane (0.67 ml) was added dropwise over 5 min. After stirring for another 15 min at -78° C., triethylamine (0.88 ml, 0.8 mmol) was added. The reaction mixture was allowed to warm to room temperature (30 min). Dichloromethane (1 ml) and water (4 ml) was added. The organic layer was extracted with water (4 ml) and brine (4 ml), dried (MgSO4), filtered and concentrated. The residue was co-concentrated with toluene (2×3 ml) to give a colorless syrup in 93% (0.37 g) yield, [α]D20 =+18.07° (c 1.4, CHCl3). 13C-NMR (CDCl3):δ200 (C-7), 97.8 (C-1), 81.6, 80.7 and 79.9 (C-2, C-3, C-4); 75.5, 74.8 and 73.2 (3×CH2OPh); 65.4 (C-5), 55.3 (OCH3); 45.6 (C-6).

Workup

  1. additionwas added dropwise over 5 min
  2. temperatureto warm to room temperature (30 min)
  3. extractionThe organic layer was extracted with water (4 ml) and brine (4 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a colorless syrup in 93% (0.37 g)
  8. customyield

Sources & evidence

ORD record
ord-dda6b37ed5ca40a68bfdd5e52d63293a
Source dataset
uspto-grants-1998_12
Patent number
US05844102

Reaction notes

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