Acetic Anhydride → beta-D-Galactose pentaacetate

HRID 263918

반응식

HRID 263918 반응식
C([O:4][C@H:5]([C@H:8]([C@H:13]([C@@H:18]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[O:19][C:20](=[O:22])[CH3:21])[O:14][C:15](=[O:17])[CH3:16])[O:9][C:10](=[O:12])[CH3:11])[CH:6]=[O:7])(=O)C.[O:28]=[CH:29][C@@H:30]([C@H]([C@H]([C@@H](CO)O)O)O)O.C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>ClC(Cl)C>[C:25]([O:24][C@@H:23]1[O:4][C@H:5]([CH2:6][O:7][C:29](=[O:28])[CH3:30])[C@H:8]([O:9][C:10](=[O:12])[CH3:11])[C@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@H:18]1[O:19][C:20](=[O:22])[CH3:21])(=[O:27])[CH3:26]

참가 물질

6

반응물 4

HCID 7918Acetic AnhydrideHCID 81232D-galactose, 2,3,4,5,6-pentaacetateHCID 517045Sodium AcetateHCID 3037556(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanal

생성물 1

HCID 94752beta-D-Galactose pentaacetate

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

The synthesis of compounds 26-31 are depicted in FIGS. 19A and 19B and are set forth in the examples hereinbelow. In this figure, the synthesis of compounds 26, 27, 28, and 36 parallels that of compounds 17, 18, 19, and 20 as set forth above and illustrated in FIG. 18. In this regard, benzyl 4,6-O-benzylidene-2-O-benzoyl-3-O-chloroacetyl-β-D-thiogalactopyranoside (compound 31) has been produced without the necessity of chromatography. D-Galactose pentaacetate 26 is produced by slurring D-galactose and about an equimolar amount (e.g., about 1.1 equivalents) of sodium acetate (NaOAc) in dichloroethane (DCE), heating to reflux and adding at least 5 equivalents of acetic anhydride (AcOAc) dropwise to the refluxing solution (about 80°-85° C.) and then maintaining the reaction system at this temperature for a sufficient period of time (about 16-32 hours) to result in formation of compound 26. This procedure optimizes the yield of β-D-galactose pentaacetate 26 and controls the exotherm of heretofore known procedures.

후처리

  1. temperatureto reflux
  2. temperaturemaintaining the reaction system at this temperature for a sufficient period of time (about 16-32 hours)

출처 및 근거

ORD 기록
ord-20dced2533344dd89a2390ac4a91878c
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646123

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