Sucrose → (2R,3R,4S,5S,6R)-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;prop-2-enoate

HRID 850693

Reaction equation

HRID 850693 reaction equation
[CH2:1]([OH:23])[C@H:2]1[O:7][C@H:6]([O:8][C@:9]2([CH2:18][OH:19])[O:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([OH:16])[C@@H:10]2[OH:17])[C@H:5]([OH:20])[C@@H:4]([OH:21])[C@@H:3]1[OH:22].COC1C=CC(O)=CC=1.[C:33]([O:37]CC1OC1)(=[O:36])[CH:34]=[CH2:35].[Al]>P([O-])([O-])([O-])=O>[CH2:1]([OH:23])[C@H:2]1[O:7][C@H:6]([O:8][C@:9]2([CH2:18][OH:19])[O:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([OH:16])[C@@H:10]2[OH:17])[C@H:5]([OH:20])[C@@H:4]([OH:21])[C@@H:3]1[OH:22].[C:33]([O-:37])(=[O:36])[CH:34]=[CH2:35]

Participants

6

Reactant 4

HCID 5988Sucrose2×HCID 7836Glycidyl acrylate2×HCID 90154-MethoxyphenolHCID 5359268Aluminum

Product 1

HCID 131721615(2R,3R,4S,5S,6R)-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;prop-2-enoate

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

Four batches of sucrose acrylate monomers were prepared. For each batch, 10 g of sucrose, 1.9 g of TAB (99%), and a small amount of p-methoxyphenol, which was used as a polymerization inhibitor, were dissolved in 20 ml phosphate buffered aqueous solution (pH 7.2, 0.05 M) in a 200 ml Erlenmeyer flask equipped with magnetic stirrer. The TAB was used as a phase transfer catalyst. Glycidyl acrylate (GA) (Lancaster Synthesis, Inc.; Windham, N.H.) was added to each batch to make sucrose:GA ratios of 1:4, 1:1.5, 1:1:5, and 1:8. The reaction was performed at room temperature with continuous stirring and the flasks were covered with aluminum foil to avoid the light.

Workup

  1. customequipped with magnetic stirrer
  2. customwas performed at room temperature

Sources & evidence

ORD record
ord-00c5568940204401afab0faf8b41193f
Source dataset
uspto-grants-2000_01
Patent number
US06018033

Linked notes

Loading…