Water → 4-O-benzyl-N-benzyloxycarbonyl-1,5-imino-1,2,5-trideoxy-D-arabino-hexitol

HRID 2050671

반응식

HRID 2050671 반응식
[CH2:1]([O:8][C@H:9]1[C@H:16]([OH:17])[CH2:15][CH2:14][N:13]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[C@@H:10]1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O.[Cl-].[NH4+]>C(O)C>[CH2:1]([O:8][C@@H:9]1[C@@H:10]([CH2:11][OH:12])[N:13]([C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19])[CH2:14][CH2:15][C@H:16]1[OH:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 1317168873-O-benzyl-N-benzyloxycarbonyl-2,6-imino-2,5,6-trideoxy-D-lyxo-hexose

생성물 1

HCID 145234464-O-benzyl-N-benzyloxycarbonyl-1,5-imino-1,2,5-trideoxy-D-arabino-hexitol수율 97%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

3-O-Benzyl-N-benzyloxycarbonyl-2,6-imino-2,5,6-trideoxy-D-lyxo-hexose (24) (364 mg, 0.986 mmol) was dissolved in ethanol (5 ml) and treated with a solution of sodium borohydride (30.0 mg, 0.784 mmol) in a 1:1 mixture of EtOH and H2O (2 ml). After 20 minutes excess ammonium chloride was added, the solution concentrated, poured into brine (15 ml) and extracted with dichloromethane (4×20 ml). The organic layers were combined, dried, filtered and evaporated to give 4-O-benzyl-N-benzyloxycarbonyl-1,5-imino-1,2,5-trideoxy-D-arabino-hexitol (355 mg, 97%) as a clear oil, [α]20D -36.7° (c, 0.22 in chloroform); νmax (film) 3380 (OH), 2910, 1665 (2×CO), 1430, 1210 and 1075 cm-1 ; 1H NMR δ 1.55-1.68 (1H, m, H-2); 2.04-2.17 (1H, m, H-2'); 2.85 (2H, bs, 2×OH); 3.40-3.57 (2H, m, H-5, H-1); 3.83-4.03 (4H, m, 6,6'-H, H-4, H-1'); 4.34 (1H, bs, H-3); 4.55, 4.72 (2H, 2×d, CH2Ph, JH,H 12.0 Hz); 5.15 (2H, s, CH2 -Z); 7.28-7.38 (10, m, 2×H-Ph). m/z: 264 (M-benzyloxy+, 100%), 91 (10%), 372 (M+H+, 5%).

후처리

  1. concentrationthe solution concentrated
  2. additionpoured into brine (15 ml)
  3. extractionextracted with dichloromethane (4×20 ml)
  4. customdried
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-31bb67cf752e4a7198a28dd9bf38326b
출처 데이터셋
uspto-grants-1991_05
특허 번호
US05013842

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