Hydrochloric Acid → 9-[4-(Diethoxyphosphorylmethoxy)-1-hydroxybut-2-oxy]guanine

HRID 345087ノート

反応式

HRID 345087 の反応式
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[N:17]=[C:16]2[C:12]([N:13]=[CH:14][N:15]2[O:18][CH:19]([CH2:29][CH2:30][O:31][CH2:32][P:33]([O:38][CH2:39][CH3:40])([O:35][CH2:36][CH3:37])=[O:34])[CH2:20][O:21][Si](C(C)(C)C)(C)C)=[C:11]([O:41]C)[N:10]=1)=O)(C)(C)C.Cl>C(O)C>[CH2:36]([O:35][P:33]([CH2:32][O:31][CH2:30][CH2:29][CH:19]([O:18][N:15]1[CH:14]=[N:13][C:12]2[C:11](=[O:41])[NH:10][C:9]([NH2:8])=[N:17][C:16]1=2)[CH2:20][OH:21])([O:38][CH2:39][CH3:40])=[O:34])[CH3:37]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 199935582-[Bis(t-butoxycarbonyl)amino]-9-[1-(t-butyldimethylsilyloxy)-4-(diethoxyphosphorylmethoxy)but-2-oxy]-6-methoxypurine

生成物 1

HCID 1363411999-[4-(Diethoxyphosphorylmethoxy)-1-hydroxybut-2-oxy]guanine収率 48%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 2-[bis(t-butoxycarbonyl)amino]-9-[1-(t-butyldimethylsilyloxy)-4-(diethoxyphosphorylmethoxy)but-2-oxy]-6-methoxypurine (415 mg, 0.57 mmol) was dissolved in ethanol (5 ml) and 5M hydrochloric acid (0.6 ml) and heated under reflux for 3.5 h. The reaction was evaporated in vacuo and the residue chromatographed on silica, eluting with chloroform-methanol 10:1, affording 9-[4-(diethoxyphosphorylmethoxy)-1-hydroxybut-2-oxy]guanine (110 mg, 48%) as a pale tan solid. νmax (KBr) 3400, 1680, 1640 and 1600 cm-1 ; δH [(CD3)2SO] 1.22 (6H, t, J7.1 Hz, 2×CH2CH3), 1.91 (2H, m, CHCH2CH2O), 3.54 (2H, m, CH2OH), 3.74 (2H, m, CH2OCH2P), 3.85 (2H, d, J8.2 Hz, CH2P), 4.03 (4H, m, 2×CH2CH3), 4.30 (1H, m, HOCH2CH), 5.01 (1H, m, D2O exchangeable OH), 6.65 (2H, br.s, D2O exchangeable, NH2); m/z (FAB+ve Ion), 428 (MNa+), 406 (MH+).

後処理

  1. temperatureunder reflux for 3.5 h
  2. customThe reaction was evaporated in vacuo
  3. customthe residue chromatographed on silica
  4. washeluting with chloroform-methanol 10:1

出典と根拠

ORDレコード
ord-029d4490a18246e8a7885b05333a6b31
出典データセット
uspto-grants-1991_10
特許番号
US05055458

反応ノート

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