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

HRID 1836224
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HRID 1836224 반응식
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]>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]
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참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 516892Sodium Bicarbonate
용매

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온도
0 °C

실험 절차

To an ice-cold suspension of Dess-Martin periodinane (50.0 g, 118 mmol) in anhydrous CH2C12 (350 mL) under argon (Ar) was added a solution of the compound from Step A (36.2 g, 75 mmol) in anhydrous CH2C12 (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.

후처리

  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

출처 및 근거

ORD 기록
ord-fcbf2e526d754d30b7652404b2ec2137
출처 데이터셋
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06777395B2

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