tert-Butyl methyl ether → 2,3,4,6-Tetra-o-acetyl-1-o-(4-carboxybutyl)-glucopyranose

HRID 2307739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2307739
[C:1]([O:4][C@@H:5]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[O:8][CH:6]1[OH:7])(=[O:3])[CH3:2].C1CCN2C(=NCCC2)CC1.C([O:43][C:44]([CH2:46][CH2:47][CH2:48][CH2:49]COS(C1C=CC(C)=CC=1)(=O)=O)=[O:45])C1C=CC=CC=1.COC(C)(C)C>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[C:1]([O:4][C@@H:5]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[O:8][CH:6]1[O:7][CH2:49][CH2:48][CH2:47][CH2:46][C:44]([OH:45])=[O:43])(=[O:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 15413tert-Butyl methyl etherHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11824227GlyTouCan:G97391RAHCID 880521145-Tosyloxy-pentanecarboxylic acid benzyl ester

Produkt 1

HCID 101146692,3,4,6-Tetra-o-acetyl-1-o-(4-carboxybutyl)-glucopyranose

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture that consists of 34.83 g (100 mmol) of 2,3,4,6-tetra-O-acetyl-glucopyranose, 1.39 g (5 mmol) of tetrabutylammonium chloride and 15.22 g (100 mmol) of DBU in 300 ml of tetrahydrofuran is cooled to 0° C. At 0° C., 54.37 g (150 mmol) of 5-tosyloxy-pentanecarboxylic acid benzyl ester, dissolved in 40 ml of tetrahydrofuran, is added in drops over 30 minutes while being stirred vigorously. It is stirred for three hours at 0° C. 300 ml of MTB (methyl-tert-butyl ether) is added, solid is filtered out, and the filtrate is evaporated to the dry state in a vacuum. The residue is taken up in 500 ml of tetrahydrofuran. 5 g of palladium (10%) on activated carbon is added thereto and hydrogenated until hydrogen absorption is completed. Then, catalyst is filtered out, it is rewashed with a little tetrahydrofuran and evaporated to the dry state in a vacuum. The residue is chromatographed on silica gel (mobile solvent: dichloromethane/n=hexane/ethanol/acetic acid=20:5:3:0.5). The product-containing fractions are concentrated by evaporation, dissolved in 400 ml of ethyl acetate, and shaken out three times with 200 ml of water. Then, the organic phase is separated and evaporated to the dry state in a vacuum.

Aufarbeitung

  1. additionis added in drops over 30 minutes
  2. stirringIt is stirred for three hours at 0° C
  3. filtrationsolid is filtered out
  4. customthe filtrate is evaporated to the dry state in a vacuum
  5. addition5 g of palladium (10%) on activated carbon is added
  6. customhydrogenated until hydrogen absorption
  7. filtrationThen, catalyst is filtered out
  8. customevaporated to the dry state in a vacuum
  9. customThe residue is chromatographed on silica gel (mobile solvent: dichloromethane/n=hexane/ethanol/acetic acid=20:5:3:0.5)
  10. concentrationThe product-containing fractions are concentrated by evaporation
  11. dissolutiondissolved in 400 ml of ethyl acetate
  12. stirringshaken out three times with 200 ml of water
  13. customThen, the organic phase is separated
  14. customevaporated to the dry state in a vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c5ba5b9e1e5246d5a458bb77e1fea32b
Quelldatensatz
uspto-grants-2004_12
Patentnummer
US06831164B2

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