1-Bromononane → (2R,3R,4R,5R)-5-(2,6-Diamino-9H-purin-9-yl)-2-(hydroxymethyl)-4-(nonyloxy)tetrahydrofuran-3-ol

HRID 264720

반응식

HRID 264720 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+].Br[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>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][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[C:4]([NH2:20])[N:3]=1

참가 물질

5

반응물 3

HCID 127421-BromononaneHCID 24758Sodium hydride2회HCID 722002-Aminoadenosine

생성물 1

HCID 15858694(2R,3R,4R,5R)-5-(2,6-Diamino-9H-purin-9-yl)-2-(hydroxymethyl)-4-(nonyloxy)tetrahydrofuran-3-ol수율 39.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

2,6-Diamino-9-(β-D-ribofuranosyl)purine (50 g, 180 mmol) was treated with sodium hydride (8.8 g, 220 mmol) and bromononane (59 g, 54.4 ml, 285 mmol) in DMF (700 ml) as per the procedure of Example 2 (the diamino compound in DMF was cooled in an ice bath during the addition of NaH) to yield 83 g of crude product. 50 g of crude product was purified by silica gel chromatography. Fraction containing 2'-O-nonyl and 3'-O-nonyl product were combined to give a 77:23 mixture (29 g) of the 2' and 3' product. Pure 2'-O-nonyl product is obtained by chromatography. 1H NMR (DMSO-d6) δ 0.95 (t, 3, CH3); 1.17 [m, 12, O--CH2 --CH2 --(CH2)6 ]; 1.42 [m, 2, O--CH2CH2 (CH2)6 ]; 3.27-3.70 (m, 2, H-5'); 3.50-3.70 [m, 2, O--CH2 (CH2)7 ]; 3.95 (m, 1, H-4'), 4.24 (m, 1, H-3'); 4.40 (m, 1, H-2'); 5.10 (d, 1, 3'-OH, J=5 Hz); 5.50 (t, 1, 5'-OH, J=6 Hz); 5.76 (s, 2, 2-NH2); 5.83 (d, 1, H-1', J=6.0 Hz); 6.81 (s, 2, 6-NH2); and 7.96 (s, 1, 8-H).

후처리

  1. customto yield 83 g of crude product
  2. custom50 g of crude product was purified by silica gel chromatography
  3. additionFraction containing 2'-O-nonyl and 3'-O-nonyl product

출처 및 근거

ORD 기록
ord-a12476facfa64baab2543d46c2048072
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646265

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