Dimethyl Sulfoxide → (2R,3R,4S)-2,3,4,6-tetrakis(benzyloxy)-5-oxohexanal

HRID 1747013Notes

Reaction equation

HRID 1747013 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:18][C@H:19]([C@@H:22]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C@H:23]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C@H:24]([OH:34])[CH2:25][O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:20][OH:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(CC)CC>C(Cl)Cl>[CH2:11]([O:18][C@H:19]([C@@H:22]([O:43][CH2:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[C@H:23]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:24](=[O:34])[CH2:25][O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH:20]=[O:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 108752501,3,4,5-Tetra-O-benzyl-D-glucitol

Product 1

HCID 11103493(2R,3R,4S)-2,3,4,6-tetrakis(benzyloxy)-5-oxohexanalYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-5 °C

Procedure

To a stirred solution of oxalyl chloride (12.8 mL, 147.7 mmol) in DCM (150 mL) was added drop wise a solution of DMSO (13.1 mL) in DCM (90 mL) over 10 min at −78° C. and then the reaction mixture was stirred at same temperature for 40 min. Then a solution of (2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)hexane-1,5-diol 2 in DCM (75 mL) was added drop wise to the reaction mixture over a period of 15 min keeping the reaction mixture below −70° C. After stifling the reaction mixture for 2 h at below −70° C., Et3N (62.15 mL, 443 mmol) was added drop wise over a period of 10 min and then the reaction mixture was allowed to warm to −5° C. over a period of 2 h. The reaction mixture was concentrated under reduced keeping the temperature below 25° C. to afford crude (2R,3R,4S)-2,3,4,6-tetrakis(benzyloxy)-5-oxohexanal 3 (18 g, 90%) as sticky yellowish oil which was used for the next step without any purification.

Workup

  1. customthe reaction mixture below −70° C
  2. customfor 2 h
  3. customat below −70° C.
  4. concentrationThe reaction mixture was concentrated
  5. customthe temperature below 25° C.

Sources & evidence

ORD record
ord-dfda9fe241924e6a844afd39917a3490
Source dataset
uspto-grants-2015_10
Patent number
US09150557B1

Reaction notes

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