HCID 18609808, compound → HCID 13386274, compound

HRID 2309258Notes

Reaction equation

HRID 2309258 reaction equation
[C:1]([O:20][CH2:21][C@H:22]1[O:27][C@H:26]([O:28][CH2:29][C@H:30]([O: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])[CH2:31][O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C@H:25]([OH:62])[C@@H:24]([OH:63])[C@H:23]1[OH:64])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OC(=O)C)(=O)C.N1C=CC=CC=1>[C:1]([O:62][C@@H:25]1[C@@H:24]([O:63][C:26](=[O:27])[CH3:25])[C@@H:23]([O:64][C:29](=[O:28])[CH3:30])[C@@H:22]([CH2:21][O:20][C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:27][C@@H:26]1[O:28][CH2:29][C@H:30]([O: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])[CH2:31][O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])(=[O:20])[CH3:2]

Participants

4

Reactant 1

HCID 18609808HCID 18609808, compound

Product 1

HCID 13386274HCID 13386274, compoundYield 192.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 7918Acetic AnhydrideSolvent

Procedure

3-O-(6-O-trityl-α-D-galactopyranosyl)-1,2-di-O-tetra-decyl-Sn-glycerol (4) (672 mg) was dissolved in acetic anhydride (3 ml) and pyridine (3 ml). The solution was stirred at room temperature for 24 hours and concentrated in vacuo. The residue was subjected to column chromatography (Wakogel C-300, 70 g) and eluted with 0.5% methanol-containing chloroform to obtain 3-O-(2,3,4-tri-O-acetyl-6-O-trityl-α-D-galactopyranosyl)-1,2-di-O-tetradecyl-Sn-glycerol (5) (740 mg, 96.4%).

Workup

  1. concentrationconcentrated in vacuo
  2. washeluted with 0.5% methanol-
  3. additioncontaining chloroform

Sources & evidence

ORD record
ord-03c56383a444415ea509b06e768fbb87
Source dataset
uspto-grants-1987_09
Patent number
US04694076

Reaction notes

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