tert-Butyl (2S,3S)-3-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl-(dimethyl)silyl]oxy}-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-tetrahydro-2-furanyl]-2-(dibenzylamino)-3-hydroxy-propanoate → HCID 59065916, 화합물

HRID 25679

반응식

HRID 25679 반응식
[C:1]([Si:5]([CH3:63])([CH3:62])[O:6][C@H:7]1[C@@H:11]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[C@H:10]([N:20]2[CH:25]=[CH:24][C:23](=[O:26])[N:22]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)[C:21]2=[O:36])[O:9][C@@H:8]1[C@@H:37]([OH:61])[C@H:38]([N:46](CC1C=CC=CC=1)CC1C=CC=CC=1)[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[NH2:46][C@@H:38]([C@@H:37]([C@@H:8]1[C@@H:7]([O:6][Si:5]([C:1]([CH3:2])([CH3:3])[CH3:4])([CH3:63])[CH3:62])[C@@H:11]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:14])[CH3:15])[C@H:10]([N:20]2[CH:25]=[CH:24][C:23](=[O:26])[N:22]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)[C:21]2=[O:36])[O:9]1)[OH:61])[C:39]([O:41][C:42]([CH3:44])([CH3:43])[CH3:45])=[O:40]

참가 물질

4

반응물 1

HCID 59065932tert-Butyl (2S,3S)-3-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl-(dimethyl)silyl]oxy}-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-tetrahydro-2-furanyl]-2-(dibenzylamino)-3-hydroxy-propanoate

생성물 1

HCID 59065916HCID 59065916, 화합물수율 21%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

tert-Butyl (2S,3S)-3-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl-(dimethyl)silyl]oxy}-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-tetrahydro-2-furanyl]-2-(dibenzylamino)-3-hydroxy-propanoate (850 mg, 0.942 mmole, obtained from Reference Example 4) was hydrogenated using 10% palladium on carbon in methanol (10 ml) under atmospheric pressure. The catalyst was removed and the volatile was removed in vacuo. The residue was chromatographed (flash column, silica gel, methylene chloride:methanol:diethyl ether=95:2:3) to give the recovered starting material (248 mg, 29%) and tert-butyl (2S,3S)-2-amino-3-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl-(dimethyl)silyl]oxy}-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-tetrahydro-2-furanyl]-3-hydroxypropanoate (141 mg, 21%) as a white amorphous solid.

후처리

  1. customThe catalyst was removed
  2. customthe volatile was removed in vacuo
  3. customThe residue was chromatographed (flash column, silica gel, methylene chloride:methanol:diethyl ether=95:2:3)

출처 및 근거

ORD 기록
ord-5da621dc1348407c9ac832980e18e9e3
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858591B2

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