Octanoic Acid → α-D-Glucopyranoside, methyl, 6-octanoate

HRID 1589778Notes

Reaction equation

HRID 1589778 reaction equation
[O:1]([CH3:13])[C@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].[C:14](O)(=[O:22])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>>[C:14]([O:12][CH2:11][C@H:9]1[O:10][C@H:2]([O:1][CH3:13])[C@H:3]([OH:4])[C@@H:5]([OH:6])[C@@H:7]1[OH:8])(=[O:22])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

3

Reactant 2

HCID 379Octanoic AcidHCID 64947methyl alpha-D-glucopyranoside

Product 1

HCID 14828956α-D-Glucopyranoside, methyl, 6-octanoateYield 33.4%

Procedure

Methyl α-D-glucopyranoside (20.0 g, 0.10 mol, prepared according to Example 6), was esterified with octanoic acid (29.7 g, 0.21 mol) by the procedure described in Example 1 using 6.0 g of an immobilized lipase (from Candida antarctica) as a catalyst. After 36 hours HPLC analysis showed 77% conversion (65% monoester, 12% diester). The reaction was stopped by filtering off the enzyme. Part of the crude product was purified by chromatography yielding 10.7 g (32.4%) of the title compound which was identified by NMR spectroscopy.

Workup

  1. filtrationby filtering off the enzyme
  2. customPart of the crude product was purified by chromatography

Sources & evidence

ORD record
ord-e977c682f69f47d2a4159cd0eeb5c359
Source dataset
uspto-grants-1993_04
Patent number
US05200328

Reaction notes

Loading…