Methanol → methyl (3S,3aS,6R,6aS)-6-(nitrooxy)hexahydrofuro[3,2-b]furan-3-yl hydrogen phosphate

HRID 222537노트

반응식

HRID 222537 반응식
Br[Si](C)(C)C.[P:6]([O:12][C@H:13]1[CH2:17][O:16][C@@H:15]2[C@H:18]([O:21][N+:22]([O-:24])=[O:23])[CH2:19][O:20][C@H:14]12)([O:10]C)([O:8][CH3:9])=[O:7].CO>C(#N)C>[P:6]([OH:10])([O:12][C@H:13]1[CH2:17][O:16][C@@H:15]2[C@H:18]([O:21][N+:22]([O-:24])=[O:23])[CH2:19][O:20][C@H:14]12)([O:8][CH3:9])=[O:7]

참가 물질

5

반응물 3

HCID 887MethanolHCID 76113BromotrimethylsilaneHCID 86652099dimethyl (3S,3aS,6R,6aS)-6-(nitrooxy)hexahydrofuro[3,2-b]furan-3-yl phosphate

생성물 1

HCID 86652098methyl (3S,3aS,6R,6aS)-6-(nitrooxy)hexahydrofuro[3,2-b]furan-3-yl hydrogen phosphate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Bromotrimethylsilane (0.191 mL, 1.47 mmol) was added to a stirred room temperature mixture of dimethyl (3S,3aS,6R,6aS)-6-(nitrooxy)hexahydrofuro[3,2-b]furan-3-yl phosphate (400 mg, 1.34 mmol) in acetonitrile (6 mL) at 0° C., and the mixture was stirred at room temperature for 1 hour. Methanol (5 mL) was added, and the solution was concentrated. The residue was purified by preparative HPLC, eluting with 10-100% acetonitrile/water+0.1% trifluoroacetic acid, to afford the title compound as a white gum. 1H NMR (500 MHz, CD3OD) δ 5.45 (tt, J=5.3, 2.6 Hz, 1H), 5.00 (q, J=5.4 Hz, 1H), 4.74 (ddd, J=9.7, 7.2, 2.8 Hz, 1H), 4.57 (d, J=4.9 Hz, 1H), 4.09 (d, J=10.5 Hz, 1H), 3.97 (dt, J=11.3, 2.5 Hz, 1H), 3.92-3.83 (m, 2H), 3.72 (d, J=11.2 Hz, 3H); LC-MS: m/z 286.0 (M+H).

후처리

  1. concentrationthe solution was concentrated
  2. customThe residue was purified by preparative HPLC
  3. washeluting with 10-100% acetonitrile/water+0.1% trifluoroacetic acid

출처 및 근거

ORD 기록
ord-2bbe7b8d394946379f25147718de0b7f
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207208B2

반응 노트

불러오는 중…