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

HRID 2050670ノート

反応式

HRID 2050670 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-a78277bd37c74358849646f6dbe02caa
出典データセット
uspto-grants-1991_05
特許番号
US05013842

反応ノート

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