Triethoxymethylsilane → (+)-Lactose

HRID 1531446Notes

Reaction equation

HRID 1531446 reaction equation
C[Si](OCC)(OCC)OCC.O.[OH:13][CH:14]1[O:33][C@H:32]([CH2:34][OH:35])[C@@H:19]([O:20][C@@H:21]2[O:29][C@H:28]([CH2:30][OH:31])[C@H:26]([OH:27])[C@H:24]([OH:25])[C@H:22]2[OH:23])[C@H:17]([OH:18])[C@H:15]1[OH:16].[SiH3]O>O.C(O)C>[OH:13][CH:14]1[O:33][C@H:32]([CH2:34][OH:35])[C@@H:19]([O:20][C@@H:21]2[O:29][C@H:28]([CH2:30][OH:31])[C@H:26]([OH:27])[C@H:24]([OH:25])[C@H:22]2[OH:23])[C@H:17]([OH:18])[C@H:15]1[OH:16]

Participants

6

Reactant 3

HCID 16241TriethoxymethylsilaneHCID 62223Lactose monohydrateHCID 142154Silanol

Product 1

HCID 440995(+)-Lactose

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

100 ml of methyltriethoxysilane are solubilized in a mixture of 80 g of water and 350 g of absolute ethanol. 1.1 kg of lactose monohydrate is then added to the solution (partially soluble), and the whole mixture is maintained under stirring at room temperature for 17 hours. The solvents are then progressively eliminated by distillation under reduced pressure (2000-2600 Pa) and moderate heat. Finally 1.12 Kg of a white pulverulent solid is obtained, which may be further transformed, by dissolution in water or in vivo, into a biologically active silanol with the same properties as the silanols from the prior art.

Workup

  1. temperatureis maintained
  2. distillationThe solvents are then progressively eliminated by distillation under reduced pressure (2000-2600 Pa) and moderate heat
  3. customFinally 1.12 Kg of a white pulverulent solid is obtained

Sources & evidence

ORD record
ord-546bc62baa6e4fc1bf7e39e1b6252577
Source dataset
uspto-grants-2001_03
Patent number
US06197986B1

Reaction notes

Loading…