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Water → [3-Hydroxy-10-(hydroxymethyl)-4',4',5',14-tetramethyl-3',9,13-trioxospiro[11,12-dithia-8,14-diazatetracyclo[8.2.2.01,8.03,7]tetradecane-5,2'-oxolane]-4-yl] acetate

HRID 1579973
ノート
印刷プレビュー

反応式

HRID 1579973 の反応式
[CH3:1][CH:2]1[O:7][C@:6]2([C@@H:11]([O:12][C:13]([CH3:15])=[O:14])[C@:10]3([OH:32])[CH2:16][C@@:17]45[S:29][S:28]SS[C@@:21]([CH2:30][OH:31])([N:22]([CH3:25])[C:23]4=[O:24])[C:19](=[O:20])[N:18]5[C@@H:9]3[CH2:8]2)[C:4](=[O:5])[C:3]1([CH3:34])[CH3:33].S(Cl)(Cl)=O.O>N1C=CC=CC=1>[CH3:1][CH:2]1[O:7][C:6]2([CH:11]([O:12][C:13]([CH3:15])=[O:14])[C:10]3([OH:32])[CH2:16][C:17]45[S:29][S:28][C:21]([CH2:30][OH:31])([N:22]([CH3:25])[C:23]4=[O:24])[C:19](=[O:20])[N:18]5[CH:9]3[CH2:8]2)[C:4](=[O:5])[C:3]1([CH3:34])[CH3:33]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 101593099HCID 101593099、化合物

生成物 1

HCID 325517[3-Hydroxy-10-(hydroxymethyl)-4',4',5',14-tetramethyl-3',9,13-trioxospiro[11,12-dithia-8,14-diazatetracyclo[8.2.2.01,8.03,7]tetradecane-5,2'-oxolane]-4-yl] acetate

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

Sirodesmin B (50 mg.) in dry pyridine (1.0 ml.) was treated with thionyl chloride (0.1 ml.) for 12 minutes at 0°C., then added to iced-water (25 ml.) and left for 15 minutes. The solution was adjusted to pH 2 with 2N.sulphuric acid, then extracted with chloroform (3 × 20 ml.). The extracts were dried over sodium sulphate, then concentrated to an oil (29.4 mg.) which was essentially Sirodesmin A but contained traces of Sirodesmin B and C. The crude product was purified by preparative t.l.c. on silica gel G.F. (solvent, formic acid: methanol: chloroform, 1:4:95) to yield Sirodesmin A as an oil (12.5 mg.).

後処理

  1. extractionsulphuric acid, then extracted with chloroform (3 × 20 ml.)
  2. dry with materialThe extracts were dried over sodium sulphate
  3. concentrationconcentrated to an oil (29.4 mg.) which
  4. customThe crude product was purified by preparative t.l.c

出典と根拠

ORDレコード
ord-1784a5d6cbe74a96a7e43b95dd352719
出典データセット
uspto-grants-1976_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US03932394

反応ノート

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