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2'-Hydroxyacetophenone → 2-acetylphenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

HRID 6048
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HRID 6048 반응식
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[C:11]([O:14][C@@H:15]1[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:19]([O:25][C:26](=[O:28])[CH3:27])[CH2:18][S:17][CH:16]1Br)(=[O:13])[CH3:12]>C(Cl)Cl.C(#N)C.[N-]1C=CN=C1.[Ag+].[Cl-].[Zn+2].[Cl-]>[C:11]([O:14][C@@H:15]1[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:19]([O:25][C:26](=[O:28])[CH3:27])[CH2:18][S:17][C@H:16]1[O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9])(=[O:13])[CH3:12]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 2

HCID 83752'-HydroxyacetophenoneHCID 113826832,3,4-Tri-o-acetyl-5-thioxylopyranosyl bromide

생성물 1

HCID 150678602-acetylphenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside수율 13.5%

시약·촉매·용매 4

HCID 3007855Zincchloride촉매HCID 10931941Silver imidazolate촉매
HCID 6342
Acetonitrile
용매
HCID 6344Dichloromethane용매

실험 절차

If the procedure described in Preparation LXXXIII is followed starting from 3.45 g (25.3.10-3 mol) of 1-(2-hydroxyphenyl)ethanone, 6 g (16.9.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide, 3 g (17.10-3 mol) of silver imidazolate and 4.6 g (33.7.10-3 mol) of zinc chloride in 90 ml of methylene chloride and 30 ml of acetonitrile, 0.92 g (yield: 13.5%) of the expected product is obtained after purification by chromatography on silica gel using a toluene/ethyl acetate mixture (6/1 v/v) as the eluent, and crystallization from ether.

후처리

  1. customIf the procedure described in Preparation LXXXIII

출처 및 근거

ORD 기록
ord-f67d5b7de822472492c840983cb533d4
출처 데이터셋
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05246961

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