Methanol → Allyl 3-O-benzyl-2-deoxy-2-palmitamido-6-O-palmitoyl-beta-D-glucopyranoside

HRID 2413043Notes

Reaction equation

HRID 2413043 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:18]([OH:19])[C@@H:17]([CH2:20][OH:21])[O:16][C@@H:11]([O:12][CH2:13][CH:14]=[CH2:15])[C@@H:10]1[NH:22][C:23](=[O:39])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:46](Cl)(=[O:62])[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61].CO>C(Cl)(Cl)Cl>[CH2:1]([O:8][C@H:9]1[C@H:18]([OH:19])[C@@H:17]([CH2:20][O:21][C:46](=[O:62])[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])[O:16][C@@H:11]([O:12][CH2:13][CH:14]=[CH2:15])[C@@H:10]1[NH:22][C:23](=[O:39])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 1049PyridineHCID 8206Palmitoyl chlorideHCID 18595873allyl 3-O-benzyl-2-deoxy-2-palmitamido-beta-D-glucopyranoside2×

Product 1

HCID 18595872Allyl 3-O-benzyl-2-deoxy-2-palmitamido-6-O-palmitoyl-beta-D-glucopyranoside

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 0.38 g. of allyl 3-O-benzyl-2-deoxy-2-palmitamido-β-D-glucopyranoside (Compound 5) in 7 ml. dry pyridine at about 15° C., was added 0.3 ml. of palmitoyl chloride. After warming and holding at room temperature for 4 hours, thin layer chromatography (5% methanol in chloroform) showed the reaction to be complete. Methanol was then added and the solvent evaporated and coevaporated with toluene. Column chromatography of the residue (5% acetone in CHCl3) yielded Compound 6.

Workup

  1. temperatureAfter warming
  2. customthe reaction
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-0b8295809f584918be665bc4683883cc
Source dataset
uspto-grants-1985_01
Patent number
US04495346

Reaction notes

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