Tetramethylsilane → alpha-D-Gal-(1->4)-beta-D-Gal-(1->4)-beta-D-GlcNAc-OEt

HRID 653341

反応式

HRID 653341 の反応式
[2H]C(S(C([2H])([2H])[2H])=O)([2H])[2H].[2H]O[2H].[Si](C)(C)(C)C.[C:19]([NH:22][C@@H:23]1[C@@H:31]([OH:32])[C@H:30]([O:33][C@@H:34]2[O:71][C@H:70]([CH2:72][O:73]C(=O)C)[C@H:45]([O:46][C@H:47]3[O:64][C@H:63]([CH2:65][O:66]C(=O)C)[C@H:58]([O:59]C(=O)C)[C@H:53]([O:54]C(=O)C)[C@H:48]3[O:49]C(=O)C)[C@H:40]([O:41]C(=O)C)[C@H:35]2[O:36]C(=O)C)[C@@H:29]([CH2:77][OH:78])[O:28][C@H:24]1[O:25][CH2:26][CH3:27])(=[O:21])[CH3:20]>>[C:19]([NH:22][C@@H:23]1[C@@H:31]([OH:32])[C@H:30]([O:33][C@@H:34]2[O:71][C@H:70]([CH2:72][OH:73])[C@H:45]([O:46][C@H:47]3[O:64][C@H:63]([CH2:65][OH:66])[C@H:58]([OH:59])[C@H:53]([OH:54])[C@H:48]3[OH:49])[C@H:40]([OH:41])[C@H:35]2[OH:36])[C@@H:29]([CH2:77][OH:78])[O:28][C@H:24]1[O:25][CH2:26][CH3:27])(=[O:21])[CH3:20]

参加物

4

反応物 3

HCID 6396TetramethylsilaneHCID 70424950Ethyl 2-acetamido-2-deoxy-4-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl)-beta-D-galactopyranosyl]-beta-D-glucopyranosideHCID 86701925HCID 86701925、化合物

生成物 1

HCID 18608320alpha-D-Gal-(1->4)-beta-D-Gal-(1->4)-beta-D-GlcNAc-OEt収率 82%

実験手順

Compound 87 (58 mg, 0.06 mmol) was O-deacetylated in methanolic sodium methoxide (0.036M, 5.5 ml) at room temperature for 21 h. The mixture was neutralized with Duolite C-26 (H) resin, filtered and concentrated. The residue was dissolved in water and lyophilized to give 88 (21 mg, 60%) with [α]D22 +25° (c 0.7, water). 1H-NMR [(CD3)2SO+D2O, 50°, Me4Si] δ inter alia 4.80 (d, 1H, J=3.5 Hz, H1"), 4.37 (d, 1H, J=8 Hz, H1 or H1'), 4.29 (d, 1H, J=7.5 Hz, H1 or H1'), 4.07 (bt, 1H, J~6.5 Hz), 1.81 (s, 3H, MeCON), 1.08 (t, 3H, J=7 Hz, CH3CH 2). 13C-NMR (D2O, TSP) δ 177.4, 106.1, 103.4, 103.1, 81.6, 80.1, 78.2, 77.7, 75.4, 75.0, 73.7, 73.6, 72.0, 71.7, 71.4, 69.1 (CH2), 63.3 (CH2), 63.2 (CH2), 62.9 (CH2), 58.1, 25.0, 17.1. b: Compound 86 (15 mg, 0.017 mmol) was O-deacetylated and worked-up as above to give 88 (8.0 mg, 81%).

出典と根拠

ORDレコード
ord-1d460277a74e40298e34c189c48169dd
出典データセット
uspto-grants-1987_06
特許番号
US04675392

関連ノート

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