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Benzyl mercaptan → (2R,3R,4S,5R)-2-{2-[(Benzylsulfanyl)methyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

HRID 2268401
ノート
印刷プレビュー

反応式

HRID 2268401 の反応式
CS(O[CH2:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[CH:12][N:13]2[C@H:16]2[C@H:20]([OH:21])[C@H:19]([OH:22])[C@@H:18]([CH2:23][O:24][CH3:25])[O:17]2)=[C:9]([NH:26][CH2:27][CH:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:8]=1)(=O)=O.[C:41]1([CH2:47][SH:48])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C(N(CC)CC)C>ClCCl>[CH2:47]([S:48][CH2:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[CH:12][N:13]2[C@H:16]2[C@H:20]([OH:21])[C@H:19]([OH:22])[C@@H:18]([CH2:23][O:24][CH3:25])[O:17]2)=[C:9]([NH:26][CH2:27][CH:28]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[N:8]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 7509Benzyl mercaptanHCID 8471TriethylamineHCID 59975278{9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonate

生成物 1

HCID 59975291(2R,3R,4S,5R)-2-{2-[(Benzylsulfanyl)methyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol収率 31.6%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

{9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonate (300 mg, 0.53 mmol) (preparation 25) was dissolved in stirred dichloromethane (4 ml) and phenylmethanethiol (0.13 ml, 1.05 mmol) and triethylamine (0.15 ml, 1.05 mmol) added. The reaction mixture was stirred for 48 hr at room temperature and then the solvent removed under reduced pressure. The residue was partitioned between methanol (100 ml) and hexane (100 ml) and the methanol layer washed with a further amount of hexane (100 ml). The solvent was then removed under reduced pressure from the methanol layer. The residue was purified by column chromatography on silica gel eluting with a solvent system of ethyl acetate:hexane (3:2) increasing in polarity to ethyl acetate:methanol (98:2). This gave title compound (100 mg) as a foam. MS: 599 (MH+).

後処理

  1. customthe solvent removed under reduced pressure
  2. customThe residue was partitioned between methanol (100 ml) and hexane (100 ml)
  3. washthe methanol layer washed with a further amount of hexane (100 ml)
  4. customThe solvent was then removed under reduced pressure from the methanol layer
  5. customThe residue was purified by column chromatography on silica gel eluting with a solvent system of ethyl acetate:hexane (3:2)
  6. temperatureincreasing in polarity to ethyl acetate:methanol (98:2)

出典と根拠

ORDレコード
ord-d4a9114221404178bd6de576db947094
出典データセット
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06326359B1

反応ノート

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