Palmitoyl chloride → HCID 15236659, compound

HRID 1440189Notes

Reaction equation

HRID 1440189 reaction equation
[C:1]([O:18][CH2:19][C@H:20]([CH2:22][O:23][C@H:24]1[O:53][C@H:52]([CH2:54][OH:55])[C@@H:43]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C@H:34]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C@H:25]1[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[OH:21])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(N(CC)CC)C.[Si:63](Cl)([C:66]([CH3:69])([CH3:68])[CH3:67])([CH3:65])[CH3:64].[C:71](Cl)(=[O:87])[CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH3:86]>C(Cl)Cl.O>[C:1]([O:18][CH2:19][C@H:20]([CH2:22][O:23][C@H:24]1[O:53][C@H:52]([CH2:54][O:55][Si:63]([C:66]([CH3:69])([CH3:68])[CH3:67])([CH3:65])[CH3:64])[C@@H:43]([O:44][CH2:45][C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[C@H:34]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C@H:25]1[O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[O:21][C:71](=[O:87])[CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH3:86])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

7

Reactant 4

HCID 8206Palmitoyl chlorideHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 15236657HCID 15236657, compound

Product 1

HCID 15236659HCID 15236659, compoundYield 86.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 200 mg (0.26 mmol) of 1-O-palmitoyl-3-O-[2,3,4-tri-O-benzyl-α-D-glucopyranosyl]-sn-glycerol, 0.2 ml of triethylamine, 100 mg of N,N-dimethylaminopyridine in 10 ml of methylene chloride is added under stirring 0.5 ml of methylene chloride solution containing 50 mg (0.33 mmol) of tert-butyldimethylsilyl chloride. The mixture is stirred at room temperature for 12 hours, and to the mixture is added 150 mg (0.55 mmol) of palmitoyl chloride. The resulting mixture is stirred for 6 hours, and after addition of 0.2 ml of water, the mixture is further stirred for 30 min. The organic portion is taken out and subjected to the post treatment. Thus treated product is purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=50:1) to give 252 mg of the captioned compound as a syrup. Yield: 86%.

Workup

  1. additionis added
  2. stirringThe resulting mixture is stirred for 6 hours
  3. stirringthe mixture is further stirred for 30 min
  4. customThus treated product is purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=50:1)

Sources & evidence

ORD record
ord-c6c891877f1c4f4caa57e07cd1d08ac5
Source dataset
uspto-grants-1996_03
Patent number
US05498527

Reaction notes

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