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Acetic Anhydride → allyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-tolylsulfonyl-alpha-D-mannopyranoside

HRID 233553
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HRID 233553 반응식
[C:1]([NH:4][C@H:5]1[C@@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@H:13]([O:19][C:20](=[O:22])[CH3:21])[C@@H:12]([CH2:23][O:24]C(=O)C)[O:11][C@@H:6]1[O:7][CH2:8][CH:9]=[CH2:10])(=[O:3])[CH3:2].C[O-].[Na+].[C:31]1([CH3:41])[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[S:37](Cl)(=[O:39])=[O:38].C(OC(=O)C)(=O)C>CO.N1C=CC=CC=1.C(Cl)Cl>[C:1]([NH:4][C@H:5]1[C@@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@H:13]([O:19][C:20](=[O:22])[CH3:21])[C@@H:12]([CH2:23][O:24][S:37]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[CH3:41])(=[O:39])=[O:38])[O:11][C@@H:6]1[O:7][CH2:8][CH:9]=[CH2:10])(=[O:3])[CH3:2]
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참가 물질

8

반응물 4

HCID 7918Acetic AnhydrideHCID 8623o-Toluenesulfonyl chlorideHCID 10942334Sodium MethoxideHCID 13968146allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-mannopyranoside

생성물 1

HCID 86749068allyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-tolylsulfonyl-alpha-D-mannopyranoside수율 44%

시약·촉매·용매 3

HCID 887Methanol용매HCID 1049Pyridine용매2회HCID 6344Dichloromethane용매2회

실험 절차

A solution of allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-mannopyranoside, prepared as described above, (6.46 g, 16.7 mmol) and methanolic NaOMe (2 mL; 1M solution) in MeOH (100 mL) was stirred for two hours at room temperature, and neutralized by addition of Dowex 50W-X8 [H+ ]. After the resin was filtered off, the filtrate was concentrated followed by coevaporation with pyridine. A solution of tolylsulfonyl chloride (3.50 g, 18.3 mmol) in pyridine (20 mL) and CH2Cl2 (30 mL) was added dropwise to a cooled solution of the residue in pyridine (30 mL) and CH2Cl2 (50 mL) at 0°-5° C. over 30 minutes, and the mixture was stirred for 10 hours at room temperature then cooled. Acetic anhydride (30 mL) was added to the mixture, and the mixture was stirred for five hours room temperature. The mixture was concentrated, and the residue was chromatographed on silica gel, with toluene EtOAc (1:2), to give allyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-tolylsulfonyl-α-D-mannopyranoside (3.68 g, 44%);

후처리

  1. additionneutralized by addition of Dowex 50W-X8 [H+ ]
  2. filtrationAfter the resin was filtered off
  3. concentrationthe filtrate was concentrated
  4. temperaturethen cooled
  5. stirringthe mixture was stirred for five hours room temperature
  6. concentrationThe mixture was concentrated
  7. customthe residue was chromatographed on silica gel, with toluene EtOAc (1:2)

출처 및 근거

ORD 기록
ord-5d37064695a24f9788dfba2a4cad1079
출처 데이터셋
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05593887

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