Chloroform → 1-propenyl 3-O-benzyl-2-deoxy-2-palmitamido-6-O-palmitoyl-beta-D-glucopyranoside

HRID 2413047Notes

Reaction equation

HRID 2413047 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:18]([OH:19])[C@@H:17]([CH2:20][O:21][C:22](=[O:38])[CH2:23][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][CH3:37])[O:16][C@@H:11]([O:12][CH2:13][CH:14]=[CH2:15])[C@@H:10]1[NH:39][C:40](=[O:56])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)CCCCCCCCCCCCCCC.C(Cl)(Cl)Cl>N1C=CC=CC=1>[CH2:1]([O:8][C@H:9]1[C@H:18]([OH:19])[C@@H:17]([CH2:20][O:21][C:22](=[O:38])[CH2:23][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][CH3:37])[O:16][C@@H:11]([O:12][CH:13]=[CH:14][CH3:15])[C@@H:10]1[NH:39][C:40](=[O:56])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 8206Palmitoyl chlorideHCID 18595872Allyl 3-O-benzyl-2-deoxy-2-palmitamido-6-O-palmitoyl-beta-D-glucopyranoside

Product 1

HCID 544293391-propenyl 3-O-benzyl-2-deoxy-2-palmitamido-6-O-palmitoyl-beta-D-glucopyranoside

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 6' (6 g., 11.0 mmol) was dissolved in dry pyridine (120 ml.), and the solution was cooled at -10°. Palmitoyl chloride (4.7 ml., 16.8 mmol) was added dropwise while the reaction mixture was stirred at -10°. After an additional 30 min. the mixture was allowed to warm up to room temperature and then stirred for 2 h. The product was isolated by conventional chloroform extraction. After purification on a column of silica gel, the yield of 7 was 7.6 g (88%).

Workup

  1. temperaturethe solution was cooled at -10°
  2. stirringstirred for 2 h
  3. customAfter purification on a column of silica gel

Sources & evidence

ORD record
ord-1e5b09fc18ad41e9bcc68fa87518d76f
Source dataset
uspto-grants-1985_01
Patent number
US04495346

Reaction notes

Loading…