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Citric Acid → 1,2-dibenzyl 1-tert.butyl 1-(hydroxymethyl)-4-methyl-1,1,2(R)-pentanetricarboxylate

HRID 1464366
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HRID 1464366 반응식
B.C(C[C:5]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[C@H:6]([C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH2:7][CH:8]([CH3:10])[CH3:9])=O.C(O)(=O)C[C:40](CC(O)=O)(C(O)=O)[OH:41]>O1CCCC1>[OH:41][CH2:40][C:5]([C:31]([O:33][C:34]([CH3:37])([CH3:35])[CH3:36])=[O:32])([C:21]([O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:22])[C@H:6]([C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH2:7][CH:8]([CH3:10])[CH3:9]
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참가 물질

5

반응물 3

HCID 311Citric AcidHCID 6331BoraneHCID 867477791,2-dibenzyl 1-tert.butyl 1-(formylmethyl)-4-methyl-1,1,2(R)-pentanetricarboxylate

생성물 1

HCID 678262291,2-dibenzyl 1-tert.butyl 1-(hydroxymethyl)-4-methyl-1,1,2(R)-pentanetricarboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

8.2 ml of a 1M solution of borane in tetrahydrofuran was added to a solution of 4.055 g of 1,2-dibenzyl 1-tert.butyl 1-(formylmethyl)-4-methyl-1,1,2(R)-pentanetricarboxylate in 40 ml of dry tetrahydrofuran. After stirring for 5 minutes, the mixture was acidified with 5% aqueous citric acid solution and was extracted twice with ethyl acetate. The combined extracts were washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and evaporate. The residue was purified by flash chromatography on silica gel using hexane/ethyl acetate for the elution. There was obtained 2.518 g of 1,2-dibenzyl 1-tert.butyl 1-(hydroxymethyl)-4-methyl-1,1,2(R)-pentanetricarboxylate in the form of a colorless oil.

후처리

  1. extractionwas extracted twice with ethyl acetate
  2. washThe combined extracts were washed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporate
  5. customThe residue was purified by flash chromatography on silica gel
  6. washfor the elution

출처 및 근거

ORD 기록
ord-5b4ba37ba90b492a9241977792604083
출처 데이터셋
uspto-grants-1994_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05304549

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