Bromotriphenylmethane → 2-[1-[[(2S,3R,4R,5S,6R)-4,5-dihydroxy-2-phenylmethoxy-6-(trityloxymethyl)oxan-3-yl]amino]ethylidene]-5,5-dimethylcyclohexane-1,3-dione

HRID 991148노트

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HRID 991148 반응식
[CH3:1][C:2]1([CH3:31])[CH2:7][C:6](=[O:8])[C:5](=[C:9]([NH:11][C@@H:12]2[C@@H:25]([OH:26])[C@H:24]([OH:27])[C@@H:23]([CH2:28][OH:29])[O:22][C@@H:13]2[O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:10])[C:4](=[O:30])[CH2:3]1.[C:32]1([C:38](Br)([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C=O)C.N1C=CC=CC=1>[CH3:1][C:2]1([CH3:31])[CH2:7][C:6](=[O:8])[C:5](=[C:9]([NH:11][C@@H:12]2[C@@H:25]([OH:26])[C@H:24]([OH:27])[C@@H:23]([CH2:28][O:29][C:38]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[O:22][C@@H:13]2[O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:10])[C:4](=[O:30])[CH2:3]1

참가 물질

4

반응물 2

HCID 11692BromotriphenylmethaneHCID 1784645382-[1-[[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-phenylmethoxyoxan-3-yl]amino]ethylidene]-5,5-dimethylcyclohexane-1,3-dione

생성물 1

HCID 1784645372-[1-[[(2S,3R,4R,5S,6R)-4,5-dihydroxy-2-phenylmethoxy-6-(trityloxymethyl)oxan-3-yl]amino]ethylidene]-5,5-dimethylcyclohexane-1,3-dione수율 66.9%

시약·촉매·용매 1

HCID 21954950Dimethylformamide pyridine용매

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온도
100 °C

실험 절차

A mixture of Benzyl 2-Deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethylamino]-α-D-glucopyranoside (100 mg, 0.23 mmol), triphenylmethylbromide (149 mg, 0.46 mmol) in DMF/pyridine 1:1 (2 ml) was stirred at 100° C. for 15 h. The reaction mixture was evaporated, the residue was taken up in CHCl3 (10 ml), washed with water (3 ml), dried over MgSO4 and concentrated. The residue was purified by chromatography using CHCl3/MeOH 10:1 as the mobile phase to give Benzyl 2-Deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethylamino]-6-O-triphenylmethyl-α-D-glucopyranoside (14) (104 mg, 64%).

후처리

  1. customThe reaction mixture was evaporated
  2. washwashed with water (3 ml)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography

출처 및 근거

ORD 기록
ord-5cf03e04292e47499f6c253e6854a1b9
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06462183B1

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