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Mannobiose → HCID 131728631、化合物

HRID 1359903
ノート
印刷プレビュー

反応式

HRID 1359903 の反応式
[CH2:1]([OH:23])[C@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@H:14]([OH:15])[C@H:13]([OH:16])[CH:12]([OH:17])[O:11][C@@H:10]2[CH2:18][OH:19])[C@@H:5]([OH:20])[C@@H:4]([OH:21])[C@@H:3]1[OH:22].[OH:24][CH:25]1[O:32][C@H:31]([CH2:33][OH:34])[C@@H:29]([OH:30])[C@H:27]([OH:28])[C@H:26]1[NH:35][C:36]([CH3:38])=[O:37]>C(Cl)Cl.C(S([O-])(=O)=O)(F)(F)F.[Ag+]>[OH:24][CH:25]1[O:32][C@H:31]([CH2:33][OH:34])[C@@H:29]([OH:30])[C@H:27]([OH:28])[C@H:26]1[NH:35][C:36]([CH3:38])=[O:37].[CH2:1]([OH:23])[C@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@H:14]([OH:15])[C@H:13]([OH:16])[CH:12]([OH:17])[O:11][C@@H:10]2[CH2:18][OH:19])[C@@H:5]([OH:20])[C@@H:4]([OH:21])[C@@H:3]1[OH:22]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 152109MannobioseHCID 439174N-Acetyl-D-Glucosamine

生成物 1

HCID 131728631HCID 131728631、化合物

試薬・触媒・溶媒 2

HCID 76223Silver(I) trifluoromethanesulfonate触媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-40 °C

実験手順

To a stirred mixture of Cp2HfCl2 (269.5 mg, 0.710 mmol), AgOTf (365.5 mg, 1.423 mmol), and molecular sieves 4A (3 g) in dry CH2Cl2 (5 mL) was added a solution of mannobiose acceptor (541.1 mg, 0.593 mmol) and GlcNAc-donor (354.0 g, 0.609 mmol) in dry CH2Cl2 (10 mL) at −78° C. The mixture was stirred for 2 h and at −40° C. for 1 h. Insoluble materials were removed by passage through silica gel and the filtrate was then diluted with EtOAc, washed with brine, aq. NaHCO3 and brine successively, dried over Na2SO4, and evaporated in vacuo. The residue was purified by silica gel column chromatography (toluene:EtOAc, 15:1-10:1) to afford compound GlcNAc-mannobiose donor (393.4 mg, 45%).

後処理

  1. customInsoluble materials were removed by passage through silica gel
  2. additionthe filtrate was then diluted with EtOAc
  3. washwashed with brine, aq. NaHCO3 and brine successively
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (toluene:EtOAc, 15:1-10:1)

出典と根拠

ORDレコード
ord-4aca3e1e5bf648b3b5485d7056a8314a
出典データセット
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07879766B2

反応ノート

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