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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Triphenylphosphine → (2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627285
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HRID 627285 반응식
OC1CN(C([O-])=O)CC=C1.[Si:11]([O:18][CH2:19][CH2:20][C:21]1[C@@H:22]([CH2:35][O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[N:23]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][C@@H:25](O)[CH:26]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:63]([O:66][NH:67][S:68]([C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][C:72]=1[N+:77]([O-:79])=[O:78])(=[O:70])=[O:69])[CH:64]=[CH2:65].N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1>[CH2:63]([O:66][N:67]([C@H:25]1[CH2:24][N:23]([C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[C@H:22]([CH2:35][O:36][Si:37]([C:40]([CH3:41])([CH3:43])[CH3:42])([CH3:39])[CH3:38])[C:21]([CH2:20][CH2:19][O:18][Si:11]([C:14]([CH3:15])([CH3:16])[CH3:17])([CH3:12])[CH3:13])=[CH:26]1)[S:68]([C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][C:72]=1[N+:77]([O-:79])=[O:78])(=[O:70])=[O:69])[CH:64]=[CH2:65]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 15497911N-(Allyloxy)-2-nitrobenzenesulfonamideHCID 218741495-hydroxy-5,6-dihydropyridine-1(2H)-carboxylateHCID 89852358(2S,5S)-tert-butyl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylate

생성물 1

HCID 131735303(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydropyridine-1(2H)-carboxylate수율 69.2%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of (2S,5S)-tert-butyl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-2-((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 281, 7.33 g, 14.61 mmol) in toluene (100 mL) at room temperature was added triphenylphosphine (4.58 g, 17.53 mmol), N-(allyloxy)-2-nitrobenzenesulfonamide (3.77 g, 14.61 mmol) and diisopropyl azodicarboxylate (3.45 mL, 17.53 mmol). The reaction mixture was stirred overnight at room temperature then concentrated. The resulting oil was triturated with hexane and filtered to remove triphenylphosphine oxide. The filtrate was concentrated onto silica gel. Silica gel chromatography (0%-20% ethyl acetate/hexanes) afforded the title compound (7.5 g, 69.2%) as a light yellow oil.

후처리

  1. concentrationthen concentrated
  2. customThe resulting oil was triturated with hexane
  3. filtrationfiltered
  4. customto remove triphenylphosphine oxide
  5. concentrationThe filtrate was concentrated onto silica gel

출처 및 근거

ORD 기록
ord-0152ac7abb524fe2a19596dee5b12c2c
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09309245B2

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