Triethylamine → Oleyl Glucose Acrylate

HRID 1816465Notes

Reaction equation

HRID 1816465 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].C(N(CC)CC)C.[CH2:20](Cl)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].C(Cl)(=[O:42])C=C>CN(C=O)C>[C:11]([OH:12])(=[O:42])[CH:9]=[CH2:7].[CH2:20]([C:2]([C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4])=[O:1])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 53677849-Octadecene, 1-chloro-

Product 1

HCID 86759674Oleyl Glucose Acrylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To glucose (10 g) in anhydrous DMF (100 ml) containing excess triethlamine was added freshly distilled oleyl chloride (1 mol. equiv.), followed by acryloyl chloride after one hour reaction. The mixture was stirred overnight and the solvent removed in vacuo. The product was purified by hexane filtration followed by chromatography on silica (1.5% methanol in methylene chloride). We have applied the same transformation technology to a pentahydroxylated sugar, glucose, as depicted in FIG. 37 to yield the glucose-based compound 31, which is a mixture of regio and stereo isomers. This material has three free hydroxyls (on average) per molecule, and has a more hydrophilic character.

Workup

  1. customreaction
  2. customthe solvent removed in vacuo
  3. filtrationThe product was purified by hexane filtration

Sources & evidence

ORD record
ord-b3e8c1bdc672466a977df94ba0fa5b9d
Source dataset
uspto-grants-2005_04
Patent number
US06884842B2

Reaction notes

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