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Triacetoxyperiodinane → 1-O-Methyl-3,5-bis-O-[(2,4-dichlorophenyl)methyl]-alpha-D-erthro-pentofuranoside-2-ulose

HRID 1270244
ノート
印刷プレビュー

反応式

HRID 1270244 の反応式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=1[CH2:31][O:32][C@@H:33]1[C@@H:39]([CH2:40][O:41][CH2:42][C:43]2[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][C:44]=2[Cl:50])[O:38][C@H:35]([O:36][CH3:37])[C@@H:34]1[OH:51]>C(Cl)Cl.CCOCC.C([O-])(O)=O.[Na+]>[Cl:23][C:24]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=1[CH2:31][O:32][C@@H:33]1[C@@H:39]([CH2:40][O:41][CH2:42][C:43]2[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][C:44]=2[Cl:50])[O:38][C@H:35]([O:36][CH3:37])[C:34]1=[O:51]
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

6

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 109944831-Methyl-3,5-bis-O-(2,4-dichlorobenzyl)-alpha-D-ribofuranoside

生成物 1

HCID 113750391-O-Methyl-3,5-bis-O-[(2,4-dichlorophenyl)methyl]-alpha-D-erthro-pentofuranoside-2-ulose収率 95%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒
2 回
HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
0 °C

実験手順

To an ice-cold suspension of Dess-Martin periodinane (50.0 g, 118 mmol) in anhydrous CH2Cl2 (350 mL) under argon (Ar) was added a solution of the compound from Step A (36.2 g, 75 mmol) in anhydrous CH2Cl2 (200 mL) dropwise over 0.5 h. The reaction mixture was stirred at 0° C. for 0.5 h and then at room temperature for 3 days. The mixture was diluted with anhydrous Et2O (600 mL) and poured into an ice-cold mixture of Na2S2O3.5H2O (180 g) in saturated aqueous NaHCO3 (1400 mL). The layers were separated, and the organic layer was washed with saturated aqueous NaHCO3 (600 mL), water (800 mL) and brine (600 mL), dried (MgSO4), filtered and evaporated to give the title compound (34.2 g) as a colorless oil, which was used without further purification in Step C below.

後処理

  1. waitat room temperature for 3 days
  2. customThe layers were separated
  3. washthe organic layer was washed with saturated aqueous NaHCO3 (600 mL), water (800 mL) and brine (600 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-f19aad5174eb4c11b4536446ebaef57a
出典データセット
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07202224B2

反応ノート

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