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

HRID 342895

반응식

HRID 342895 반응식
[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

참가 물질

5

반응물 3

HCID 124021-IodooctadecaneHCID 24758Sodium hydrideHCID 722002-Aminoadenosine

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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 solyent 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).

후처리

  1. customThe solyent 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

출처 및 근거

ORD 기록
ord-65e80d54b7644f01aea47240564a0891
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05859221

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