Trifluoroacetic acid → 3-O-benzyl-N-benzyloxycarbonyl-2,6-imino-2,5,6-trideoxy-D-lyxo-hexose

HRID 2050670노트

반응식

HRID 2050670 반응식
[CH2:1]([O:8][C@H:9]1[C@H:15]2[CH2:16][CH2:17][NH:18][C@@H:10]1[C@@H:11]([O:14]2)[O:12]C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)[C:21]([OH:23])=[O:22]>O>[CH2:1]([O:8][C@H:9]1[C@H:15]([OH:14])[CH2:16][CH2:17][N:18]([C:21]([O:23][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:22])[C@@H:10]1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 14523439methyl 3-O-benzyl-2,6-imino-2,5,6-trideoxy-beta-D-lyxo-hexofuranoside

생성물 1

HCID 1317168873-O-benzyl-N-benzyloxycarbonyl-2,6-imino-2,5,6-trideoxy-D-lyxo-hexose수율 87%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of methyl 3-O-benzyl-2,6-imino-2,5,6-trideoxy-β-D-lyxo-hexofuranoside (23β) (762 mg, 2.06 mmol) in a 1:1 mixture of trifluoroacetic acid and water (20 ml) was stirred at room temperature for 20 minutes. The solvents were removed in vacuo and the crude material purified by flash chromatography (ethyl acetate-hexane 1:2) to give 3-O-benzyl-N-benzyloxycarbonyl-2,6-imino-2,5,6-trideoxy-D-lyxo-hexose (640 mg, 87%) as a clear oil, [α]20D -17.2° (c, 0.73 in chloroform); νmax (film) 3400 (OH), 2920, 1690 (C=O), 1410, 1345 and 1060 cm-1 ; 1H NMR δ 1.50-1.71 (1H, m, H-5); 1.80 (1H, bs, OH); 2.02-2.20 (1H, m, H-5'); 3.08-3.27 (1H, m, H-6); 3.94-4.20 (2H, m, 6-H, H-3); 4.25-4.85 (4H, m, H-2, H-4, CH2 -Ph); 5.05-5.18 (2H, m, CH2 -Z); 5.50, 5.53 (0.75H, 2×s, H-1-hemiacetal); 7.20-7.40 (10H, m, 2×H-Ph); 9.68 (0.25H, s, H-1-aldehyde). 13C NMR δ 24.17 (t, C-5); 38.10 (t, C-6); 57.26, 57.77 (2×d, C-2); 67.30, 67.48, 67.58 (3×t, CH2 -Z); 71.38, 71.84, 72.12 (3×t, CH2Ph); 74.00, 74.63, 74.76 (3×d, C-3, C-4); 98.72, 98.88, 198.17 (3×d, C-1); 127.35, 127.58, 127.85, 128.01, 128.23, 128.63 (6×d, HC-Ph); 136.51, 136.62, 136.73, 137.46, 155.60 (s, C=O-Z); 137.74, 137.88 (6×s, C-Ph). m/z: 91 (100%), 262 (20%), 370 (M+H+, 15%). (Found C, 68.68; H, 6.40; N, 3.71. C21H23NO5 requires C, 68.28; H, 6.28; N, 3.79).

후처리

  1. customThe solvents were removed in vacuo
  2. customthe crude material purified by flash chromatography (ethyl acetate-hexane 1:2)

출처 및 근거

ORD 기록
ord-a78277bd37c74358849646f6dbe02caa
출처 데이터셋
uspto-grants-1991_05
특허 번호
US05013842

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