Ethyl Acetate → D-(+)-Glucal

HRID 877870

反応式

HRID 877870 の反応式
C([O:4][C@H:5]1[C@H:10]([O:11]C(=O)C)[C@@H:9]([CH2:15][O:16]C(=O)C)[O:8][CH:7]=[CH:6]1)(=O)C.C[O-].[Na+].CCOC(C)=O>CO>[O:8]1[C@H:9]([CH2:15][OH:16])[C@@H:10]([OH:11])[C@H:5]([OH:4])[CH:6]=[CH:7]1

参加物

5

反応物 3

HCID 8857Ethyl Acetate2 回HCID 688303Tri-O-acetyl-D-glucalHCID 10942334Sodium Methoxide

生成物 1

HCID 2734736D-(+)-Glucal

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

The Tri-O-Acetyl-D-Glucal [SM-A](100 g, 367 mmol) is dissolved in dry MeOH [1.5 L], and then NaOMe (110 mmol, 5.95 g) is added into reaction mixture. Within about 20 minutes, TLC (40% EtOAc/60% hexanes & 100% EtOAc) confirmed de-acetylated glucal. The reaction is quenched with 50WX4 cation exchange resin until pH is near 7.0 by pH strip paper. The mixture is filtered and evaporated to dryness under vacuum to yield syrupy glucal intermediate IntA1(59 g). Theoretical yield 100 g×(146/272) 53.7 g TLC IntA1Rf=0.1, SiO2, 100% Ethyl Acetate

後処理

  1. customThe reaction is quenched with 50WX4 cation exchange resin until pH
  2. filtrationThe mixture is filtered
  3. customevaporated to dryness under vacuum

出典と根拠

ORDレコード
ord-a34bf769c1bc49bcba050160bf95bac6
出典データセット
uspto-grants-2015_03
特許番号
US08987430B2

関連ノート

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