2,3,4,6-Tetrakis-O-(phenylmethyl)-D-galactopyranose → 2,3,4,6-Tetrakis-O-(phenylmethyl)-D-galactitol

HRID 1025548

반응식

HRID 1025548 반응식
[CH2:1]([O:8][C@@H:9]1[C@@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:13]([CH2:32][O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:12][CH:10]1[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[CH2:1]([O:8][C@H:9]([C@H:15]([C@H:14]([C@@H:13]([CH2:32][O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[OH:12])[O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:10][OH:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 27341542,3,4,6-Tetrakis-O-(phenylmethyl)-D-galactopyranoseHCID 4311764Sodium borohydride

생성물 1

HCID 100075242,3,4,6-Tetrakis-O-(phenylmethyl)-D-galactitol수율 91%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
0 °C

실험 절차

2,3,4,6-Tetra-O-benzyl-D-galactopyranose (107 g) was dissolved in ethanol (0.6 L) and, whilst stirring at 0° C., sodium borohydride (31 g) was added. After stirring overnight TLC analysis indicated completion of the reaction. The ethanol solution was partitioned between water (3 L) and ether (1.5 L). The organic phase was dried (Na2SO4), filtered and concentrated. The resulting oil was purified by flash chromatography (gradient elution using 20→50% ethyl acetate/petroleum ether) and then crystallised from a mixture of ethyl acetate/petroleum ether to give 2,3,4,6-tetra-O-benzyl-D-galactitol (97 g, 91%) as a white solid. 1H NMR (CDCl3): δ 2.4 (1H, bs), 3.35 (1H, bs), 3.55 (2H, m), 3.8 (3H, m), 3.9 (2H, m), 4.1 (1H, m), 4.4-4.8 (8H, m, OCH2Ph), 7.2-7.4 (20H, m, ArH). Mass spectrum: m/z 543 (M+H)+ 565 (M+Na)+.

후처리

  1. stirringAfter stirring overnight TLC analysis
  2. customcompletion of the reaction
  3. customThe ethanol solution was partitioned between water (3 L) and ether (1.5 L)
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting oil was purified by flash chromatography (gradient elution using 20→50% ethyl acetate/petroleum ether)
  8. customcrystallised from a mixture of ethyl acetate/petroleum ether

출처 및 근거

ORD 기록
ord-7df2f95ae1f34e4ca47f569ec9755811
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729099B2

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