Bromotrimethylsilane → (R)-9-[3-Hydroxy-2-(phosphonomethoxy)propoxy]adenine

HRID 6268

反応式

HRID 6268 の反応式
C([O:3][P:4]([CH2:9][O:10][C@H:11]([CH2:24][OH:25])[CH2:12][O:13][N:14]1[CH:22]=[N:21][C:20]2[C:15]1=[N:16][CH:17]=[N:18][C:19]=2[NH2:23])([O:6]CC)=[O:5])C.C[Si](Br)(C)C>CN(C=O)C>[OH:25][CH2:24][C@@H:11]([O:10][CH2:9][P:4]([OH:5])([OH:6])=[O:3])[CH2:12][O:13][N:14]1[CH:22]=[N:21][C:20]2[C:15]1=[N:16][CH:17]=[N:18][C:19]=2[NH2:23]

参加物

4

反応物 2

HCID 76113BromotrimethylsilaneHCID 54312423(R)-9-[2-(diethoxyphosphorylmethoxy)-3-hydroxypropoxy)adenine

生成物 1

HCID 54431838(R)-9-[3-Hydroxy-2-(phosphonomethoxy)propoxy]adenine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of (R)-9-[2-(diethoxyphosphorylmethoxy)-3-hydroxypropoxy)adenine (0.16 g, 0.43 mmol) in dry DMF (3 ml) was added trimethylsilyl bromide (0.56 ml, 4.3 mmol) and the solution stirred at ambient temperature for 4 hours. The solvent was removed under reduced presence and the residue co-evaporated with acetone/water 1:1 (x3). The solid residue was crystallised from acetone/water (0.1 g, 77%), m.p. 200°-205°. UV: λmax (EtOH), 260 (11,800) nm. IR: νmax (KBr) 3449, 3400, 3199, 3105, 2951, 2897, 1711, 1680, 1612, 1569, 1467, 1420, 1355, 1330, 1305, 1244, 1216, 1128, 1080, 924, 866 cm-1. 1H NMR: δH [(CD3)2SO]3.54 (2H, m, CH2OH), 3.70-3.85 (3H, m, OCH2P, CH), 4.36 (1H, dd, J=11 Hz, J=7 Hz, NOCHB), 4.55 (1H, dd, J=11 Hz, J=3 Hz, NOCHA), 7.51 (2H, br.s, D2O exchangeable NH2), 8.17 (1H, s, H-2 or H-8), 8.50 (1H, s, H-2 or H-8), 3.5-7.0 (3H, broad, PO(OH)2, OH). Found: C, 32.07; H, 4.73; N, 20.46%. C9H14N5O5P 1 H2O requires: C, 32.05; H, 4.78; N, 20.76%. m/z: (FAB, thioglycerol matrix) 320 (MH+). [α]D25 (0.1M NaOH)-11.5° (c=0.2).

後処理

  1. customThe solvent was removed
  2. customThe solid residue was crystallised from acetone/water (0.1 g, 77%), m.p. 200°-205°
  3. custom[α]D25 (0.1M NaOH)-11.5° (c=0.2)

出典と根拠

ORDレコード
ord-b20bae2f00b74399b5f10481617ec119
出典データセット
uspto-grants-1993_09
特許番号
US05247085

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