Triphenylphosphine → methyl 4-[(3aR,4R,6R,6aR)-6-({[bis(benzyloxy)phosphoryl]oxy}methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3-oxo-3,4-dihydro-2-pyrazinecarboxylate

HRID 392310

반응식

HRID 392310 반응식
[OH:1][CH2:2][C@@H:3]1[C@H:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][C@H:6]2[C@H:5]([N:13]2[CH:18]=[CH:17][N:16]=[C:15]([C:19]([O:21][CH3:22])=[O:20])[C:14]2=[O:23])[O:4]1.[P:24]([O-])([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>N1C=CC=CC=1>[CH2:27]([O:26][P:24]([O:1][CH2:2][C@@H:3]1[C@H:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][C@H:6]2[C@H:5]([N:13]2[CH:18]=[CH:17][N:16]=[C:15]([C:19]([O:21][CH3:22])=[O:20])[C:14]2=[O:23])[O:4]1)([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:25])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 4193600DibenzylphosphateHCID 60126642HCID 60126642, 화합물

생성물 1

HCID 69759751methyl 4-[(3aR,4R,6R,6aR)-6-({[bis(benzyloxy)phosphoryl]oxy}methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3-oxo-3,4-dihydro-2-pyrazinecarboxylate수율 102.9%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

In 4 mL of pyridine was dissolved 0.22 g of methyl 4-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3-oxo-3,4-dihydro-2-pyrazinecarboxylate. Then, 0.17 g of dibenzyl phosphate, 0.40 g of triphenylphosphine and 0.30 mL of diisopropyl azodicarboxylate were successively added and stirred at room temperature for 15 hours, and the solvent was removed under reduced pressure. By purifying the residue by column chromatography [eluent: ethyl acetate], 0.37 g of methyl 4-[(3aR,4R,6R,6aR)-6-({[bis(benzyloxy)phosphoryl]oxy}methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3-oxo-3,4-dihydro-2-pyrazinecarboxylate was obtained as an orange-colored solid product.

후처리

  1. customthe solvent was removed under reduced pressure
  2. customBy purifying the residue by column chromatography [eluent: ethyl acetate]

출처 및 근거

ORD 기록
ord-93e88e7c6186441da570a7c73aa12fcd
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06800629B2

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