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Iodine → 2,5-Anhydro-4,6-dideoxy-1-O-[(1,1-dimethylethyl)diphenylsilyl]-6-iodo-D-arabino-hexitol

HRID 1600140
ノート
印刷プレビュー

反応式

HRID 1600140 の反応式
[CH3:1][C:2]([Si:5]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[O:6][CH2:7][CH:8]([OH:14])[CH:9]([OH:13])[CH2:10][CH:11]=[CH2:12])([CH3:4])[CH3:3].C(=O)(O)[O-].[Na+].[I:32]I>C(OCC)C.O>[CH3:4][C:2]([Si:5]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[O:6][CH2:7][C@H:8]1[O:14][C@H:11]([CH2:12][I:32])[CH2:10][C@H:9]1[OH:13])([CH3:1])[CH3:3]
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 807IodineHCID 516892Sodium BicarbonateHCID 220709881-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-5-hexene-2,3-diol

生成物 1

HCID 677073192,5-Anhydro-4,6-dideoxy-1-O-[(1,1-dimethylethyl)diphenylsilyl]-6-iodo-D-arabino-hexitol

試薬・触媒・溶媒 1

HCID 21584184Diethylether water溶媒

実験手順

A 0° C. solution of 14.67 g of product from Example 274 in 200 ml of3:1 diethyl ether/water is treated with 4.99 g of sodium bicarbonate and 15.07 of iodine. The reaction mixture is stirred vigorously for 24 hours at room temperature, quenched with 15 ml of saturated sodium sulfite, and diluted with 100 ml of water. the reaction mixture is extracted with diethyl ether, dried, concentrated in vacuo, and purified by chromatography (silica gel: 0-10% ethyl acetate/hexane) to give 15.0 g of the desired product.

後処理

  1. customquenched with 15 ml of saturated sodium sulfite
  2. additiondiluted with 100 ml of water
  3. extractionthe reaction mixture is extracted with diethyl ether
  4. customdried
  5. concentrationconcentrated in vacuo
  6. custompurified by chromatography (silica gel: 0-10% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-bf1b8753d0a14406b8ab0613e6984871
出典データセット
uspto-grants-1998_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05744465

反応ノート

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