1-Iodooctadecane → 2,6-Diamino-9-(2-O-octadecyl-beta-D-ribofuranosyl)purine

HRID 363242

反応式

HRID 363242 の反応式
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]2[OH:13])=[C:4]([NH2:20])[N:3]=1.[H-].[Na+].I[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>CN(C=O)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]2[O:13][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH3:24])=[C:4]([NH2:20])[N:3]=1

参加物

5

反応物 3

HCID 124021-IodooctadecaneHCID 24758Sodium hydrideHCID 722002-Aminoadenosine

生成物 1

HCID 117311872,6-Diamino-9-(2-O-octadecyl-beta-D-ribofuranosyl)purine収率 11.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2,6-Diamino-9-(β-D-ribofuranosyl) purine (50 g, 180 mmol) and sodium hydride (7 g) in DMF (1 L) were heated to boiling for 2 hr. Iodooctadecane (100 g) was added at 150° C. and the reaction mixture allowed to cool to RT. The reaction mixture was stirred for 11 days at RT. The solvent was evaporated and the residue purified by silica gel chromatography. The product was eluted with 5% MeOH/CH2Cl2. The appropriate fractions were evaporated to yield the product (11 g). 1H NMR (DMSO-d6) δ 0.84 (t, 3, CH2), 1.22 (m, 32, O-CH2 --CH2 --(CH2)16), 1.86 (m, 2, O-CH2CH2), 3.25 (m, 2, O-CH2), 3.93 (d, 1, 4'H), 4.25 (m, 1,3'H), 4.38 (t, 1,2'H), 5.08 (d, 1, 3'-OH), 5.48 (t, 1,5'-OH), 5.75 (s, 2,6-NH2), 5.84 (d, 1, 1'-H), 6.8 (s, 2,2-NH2), and 7.95 (s, 1,8-H).

後処理

  1. customThe solvent was evaporated
  2. customthe residue purified by silica gel chromatography
  3. washThe product was eluted with 5% MeOH/CH2Cl2
  4. customThe appropriate fractions were evaporated

出典と根拠

ORDレコード
ord-78e8ff4bd61e44b2b74f2edc44574ef4
出典データセット
uspto-grants-1999_02
特許番号
US05872232

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