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Acetic Acid → 2,3,4-Tri-O-acetyl-6-deoxy-6-phthalimido-alpha-D-galactopyranosyl bromide

HRID 1155297
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HRID 1155297 반응식
C(O[C:5]1([N:24]2[C:28](=[O:29])[C:27]3=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]3[C:25]2=[O:34])O[C@H](C)[C@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]1[O:7][C:8](=O)[CH3:9])(=O)C.[BrH:35].[C:36]([OH:39])(=[O:38])[CH3:37]>ClCCl>[C:36]([O:39][C@@H:9]1[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@@H:6]([CH2:5][N:24]2[C:25](=[O:34])[C:26]3=[CH:33][CH:32]=[CH:31][CH:30]=[C:27]3[C:28]2=[O:29])[O:7][C@@H:8]1[Br:35])(=[O:38])[CH3:37]
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참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 542334551,2,3,4-tetra-O-acetyl-6-deoxy-phthalimido-D-galactopyranose

생성물 1

HCID 541665552,3,4-Tri-O-acetyl-6-deoxy-6-phthalimido-alpha-D-galactopyranosyl bromide수율 91%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 1,2,3,4-tetra-O-acetyl-6-deoxy-phthalimido-D-galactopyranose (4.2 g.) in dichloromethane (2 ml.) is treated with 30-32% hydrobromic acid in glacial acetic acid (10 ml.) for 1 hour. The reaction mixture is poured into ice-water, and the product is immediately extracted with dichloromethane. The organic layer is washed with cold aqueous sodium hydrogencarbonate and cold water, dried, and evaporated in vacuo to give the title compound as a syrup (4.0 g., 91%); n.m.r. (chloroform-d); δ 6.63 (d, J1,2 4.0 Hz, H-1), 7.58-7.90 (4 aromatic), 1.96, 2.07, and 2.13 (3 OAc).

후처리

  1. extractionthe product is immediately extracted with dichloromethane
  2. washThe organic layer is washed with cold aqueous sodium hydrogencarbonate and cold water
  3. customdried
  4. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-d8100fe71ede450cbdd8c141a29adfae
출처 데이터셋
uspto-grants-1981_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04301152

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