3-Cyanophenol → 3-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

HRID 6044

반응식

HRID 6044 반응식
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[CH2:8][S:7][CH:6]1Br)(=[O:3])[CH3:2].[OH:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[C:24]#[N:25]>C1(C)C=CC=CC=1.C(#N)C.[O-2].[Zn+2]>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[CH2:8][S:7][C@H:6]1[O:20][C:21]1[CH:28]=[CH:27][CH:26]=[C:23]([C:24]#[N:25])[CH:22]=1)(=[O:3])[CH3:2]

참가 물질

6

반응물 2

HCID 133943-CyanophenolHCID 113826832,3,4-Tri-o-acetyl-5-thioxylopyranosyl bromide

생성물 1

HCID 150678563-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside수율 25%

시약·촉매·용매 3

HCID 3007857Zinc Oxide촉매HCID 1140Toluene용매HCID 6342Acetonitrile용매

실험 절차

If the procedure described in Preparation LXXVIII is followed starting from 0.5 g (1.4.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide, 0.25 g (2.1.10-3 mol) of 3-hydroxybenzonitrile and 170 mg (2.1.10-3 mol) of zinc oxide (ZnO) in 4 ml of anhydrous toluene and 4 ml of acetonitrile, 138 mg (yield: 25%) of the expected product are obtained after purification by chromatography on silica gel using a hexane/ethyl acetate mixture (2/1 v/v) as the eluent, and precipitation in ether.

후처리

  1. customIf the procedure described in Preparation LXXVIII

출처 및 근거

ORD 기록
ord-de6b93c29d3a4007a7f8a9a45c1c7379
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246961

연결된 노트

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