Water → Phenyl 6-O-(4-azido-3-chlorobenzyl)-1-thio-beta-D-glucopyranoside

HRID 610445노트

반응식

HRID 610445 반응식
[N:1]([C:4]1[CH:55]=[CH:54][C:7]([CH2:8][O:9][CH2:10][C@H:11]2[O:23][C@@H:15]([S:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C@H:14]([O:24]CC3C=CC(OC)=CC=3)[C@@H:13]([O:34]CC3C=CC(OC)=CC=3)[C@@H:12]2[O:44]CC2C=CC(OC)=CC=2)=[CH:6][C:5]=1[Cl:56])=[N+:2]=[N-:3].O.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.O=C1O[C@H]([C@H](CO)O)C(O)=C1O>ClCCl>[N:1]([C:4]1[CH:55]=[CH:54][C:7]([CH2:8][O:9][CH2:10][C@H:11]2[O:23][C@@H:15]([S:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C@H:14]([OH:24])[C@@H:13]([OH:34])[C@@H:12]2[OH:44])=[CH:6][C:5]=1[Cl:56])=[N+:2]=[N-:3]

참가 물질

6

반응물 4

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 15433387Phenyl 6-O-(4-azido-3-chlorobenzyl)-2,3,4-tri-O-(4-methoxybenzyl)-1-thio-beta-D-glucopyranosideHCID 54670067L-Ascorbic Acid

생성물 1

HCID 54482702Phenyl 6-O-(4-azido-3-chlorobenzyl)-1-thio-beta-D-glucopyranoside수율 86%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of phenyl 6-O-(4-azido-3-chlorobenzyl)-2,3,4-tri-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (9) (1.24 g, 1.55 mmol) in dichloromethane (10 ml) were added water (0.5 ml) and DDQ (1.41 g, 6.21 mmol), and the resulting mixture was stirred at room temperature for 3 hr. Thereto was added 5% aqueous L-ascorbic acid solution, and the mixture was stirred for a while, and extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel column chromatography (eluent; dichloromethane:ethyl acetate=1:3) to give phenyl 6-O-(4-azido-3-chlorobenzyl)-1-thio-β-D-glucopyranoside (10) (584 mg, yield 86%) as yellow crystals.

후처리

  1. stirringthe mixture was stirred for a while
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue obtained
  7. customwas purified by silica gel column chromatography (eluent; dichloromethane:ethyl acetate=1:3)

출처 및 근거

ORD 기록
ord-3524a53505d044a9b9b43dca15108622
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998595

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