Tin tetrachloride → HCID 68700275, compound

HRID 2260960Notes

Reaction equation

HRID 2260960 reaction equation
[C:1]([O:4][C@@H:5]1[O:22][CH2:21][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].[Sn](Cl)(Cl)(Cl)Cl.[CH3:28][CH: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])[CH2:30][CH2:31]CCO.O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[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])[CH2:21][O:22][C@H:5]1[O:4][CH2:1][CH2:2][CH2:31][CH2:30][CH: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 4

HCID 24287Tin tetrachlorideHCID 28172551,2,3,4-Tetra-O-acetyl-beta-D-xylopyranoseHCID 86239097HCID 86239097, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 68700275HCID 68700275, compoundYield 15.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Conditions

Temperature
0 °C

Procedure

Under an argon atmosphere, 318 mg of β-xylose tetraacetate was dissolved in 6 ml of dry methylene chloride, and the solution was cooled to 0° C. A solution of 0.12 ml of tin tetrachloride dissolved in 1 ml of methylene chloride was added dropwise thereto, the mixture was agitated at room temperature for 20 minutes, and then cooled to −10° C. A solution of 326.6 mg of 5,9,13,17-tetramethyloctadecanol in 1 ml of methylene chloride was added dropwise thereto, and the mixture was agitated for 4 hours. A sodium bicarbonate water was added to the reaction solution and extraction was carried out 3 times with methylene chloride. The extract was washed with water and dried over anhydrous sodium sulfate. After the filtration, the resultant was concentrated, and the concentrate was purified by column chromatography to obtain 93 mg of 1-O-(5,9,13,17-tetramethyloctadecyl)-β-D-xylopyranoside triacetate.

Workup

  1. additionwas added dropwise
  2. temperaturecooled to −10° C
  3. stirringthe mixture was agitated for 4 hours
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter the filtration
  7. concentrationthe resultant was concentrated
  8. customthe concentrate was purified by column chromatography

Sources & evidence

ORD record
ord-38c03aef715b4e618561931db66fc730
Source dataset
uspto-grants-2010_12
Patent number
US07846903B2

Reaction notes

Loading…