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

HRID 1464366
ノート
印刷プレビュー

反応式

HRID 1464366 の反応式
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]
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 311Citric AcidHCID 6331BoraneHCID 867477791,2-dibenzyl 1-tert.butyl 1-(formylmethyl)-4-methyl-1,1,2(R)-pentanetricarboxylate

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5b4ba37ba90b492a9241977792604083
出典データセット
uspto-grants-1994_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05304549

反応ノート

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