Allyl Alcohol → allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-mannopyranoside

HRID 233552노트

반응식

HRID 233552 반응식
[OH:1][CH:2]1[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@@H:3]1[NH:12][C:13]([CH3:15])=[O:14].CC(O[C:20]([CH3:22])=[O:21])=O.[CH2:23]([OH:26])[CH:24]=C>N1C=CC=CC=1.C[N+]([O-])=O>[C:13]([NH:12][C@H:3]1[C@@H:4]([O:5][C:23](=[O:26])[CH3:24])[C@H:6]([O:7][C:2](=[O:1])[CH3:3])[C@@H:8]([CH2:10][O:11][C:20](=[O:21])[CH3:22])[O:9][C@@H:2]1[O:1][CH2:8][CH:6]=[CH2:4])(=[O:14])[CH3:15]

참가 물질

6

반응물 3

HCID 7858Allyl AlcoholHCID 7918Acetic AnhydrideHCID 439281N-Acetyl-D-Mannosamine

생성물 1

HCID 13968146allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-mannopyranoside

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6375Nitromethane용매

실험 절차

A solution of ManNAc (5.0 g, 2.6 mmol), and Ac2O (10 mL) in pyridine (20 mL) was stirred for 10 hours at room temperature, and the mixture was concentrated, followed by coevaporation with toluene. A solution of the residue, allyl alcohol (2.63 g, 45.2 mmol; 3.1 mL), BF3 ·OEt2 (1.60 g, 11.3 mmol; 1.39 mL) in CH3NO2 (150 mL) was gently refluxed for 2.5 hours. After cooling, the mixture was concentrated. The residue was chromatographed on silica gel, with toluene-EtOAc (1:2) to give allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-mannopyranoside in 6.47 g (74 percent);

후처리

  1. concentrationthe mixture was concentrated
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated
  4. customThe residue was chromatographed on silica gel, with toluene-EtOAc (1:2)

출처 및 근거

ORD 기록
ord-120338c6e35643ec91e004399dce0573
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05593887

반응 노트

불러오는 중…