Ethyl Acetate → D-(+)-Glucal

HRID 877870

반응식

HRID 877870 반응식
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

참가 물질

5

반응물 3

HCID 8857Ethyl Acetate2회HCID 688303Tri-O-acetyl-D-glucalHCID 10942334Sodium Methoxide

생성물 1

HCID 2734736D-(+)-Glucal

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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

후처리

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

출처 및 근거

ORD 기록
ord-a34bf769c1bc49bcba050160bf95bac6
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987430B2

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