Triethylamine → HCID 70872980, compound

HRID 2369279Notes

Reaction equation

HRID 2369279 reaction equation
[C:1]([O:4][C@@H:5]1[O:22][C@H:21]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=O)[CH3:2].[CH3:28][C:29]([CH2:35][CH2:36][CH2:37][CH:38]([CH3:50])[CH2:39][CH2:40][CH2:41][CH:42]([CH3:49])[CH2:43][CH2:44][CH2:45][CH:46]([CH3:48])[CH3:47])=[CH:30][CH2:31]CCO.C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[C:8]([O:7][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@@H:21]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[O:22][CH:5]1[O:4][CH2:1][CH2:2][CH2:31][CH:30]=[C:29]([CH3:28])[CH2:35][CH2:36][CH2:37][CH:38]([CH3:50])[CH2:39][CH2:40][CH2:41][CH:42]([CH3:49])[CH2:43][CH2:44][CH2:45][CH:46]([CH3:48])[CH3:47])(=[O:10])[CH3:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2724702beta-D-Glucose pentaacetateHCID 86672617HCID 86672617, compound

Product 1

HCID 70872980HCID 70872980, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

3.0 g (7.7 mmol) of β-D-Glucose pentaacetate and 3.24 g (9.99 mmol) of 5,9,13,17-tetramethyloctadec-4-en-1-ol were dissolved in dry acetonitrile (8 mL). 1.95 mL (15.4 mmol) of boron trifluoride diethyl etherate complex was added to the solution with cooling on ice. The reaction mixture was allowed to warm up slowly to room temperature while being stirred overnight before addition of 3.2 mL (23 mmol) of triethylamine at 0° C. The resulting solution was diluted with ethyl acetate, and washed with water, 1M hydrochloric acid, saturated sodium bicarbonate aqueous solution, and saturated brine, successively, and dried over sodium sulfate. After filtration, the filtrate was concentrated to obtain 1-O-(5,9,13,17-tetramethyloctadec-4-enyl)-D-glucopyranoside tetraacetate as a crude product.

Workup

  1. addition1.95 mL (15.4 mmol) of boron trifluoride diethyl etherate complex was added to the solution
  2. temperaturewith cooling on ice
  3. washwashed with water, 1M hydrochloric acid, saturated sodium bicarbonate aqueous solution, and saturated brine
  4. dry with materialsuccessively, and dried over sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c589fe0754fd4be19d2d31d446e3c423
Source dataset
uspto-grants-2014_04
Patent number
US08703922B2

Reaction notes

Loading…