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

HRID 1025548

Reaction equation

HRID 1025548 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-7df2f95ae1f34e4ca47f569ec9755811
Source dataset
uspto-grants-2014_05
Patent number
US08729099B2

Linked notes

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