Water → 3,4,6-Tri-O-acetyl-2-deoxy-D-glucopyranose

HRID 653758Notes

Reaction equation

HRID 653758 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[O:8][CH:7]=[CH:6]1)(=[O:3])[CH3:2].[OH2:20].[Br-].[Li+].O>C(#N)C>[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[O:8][CH:7]([OH:20])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 688303Tri-O-acetyl-D-glucalHCID 23702478Lithium bromide hydrate

Product 1

HCID 117482783,4,6-Tri-O-acetyl-2-deoxy-D-glucopyranoseYield 66.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3,4,6-tri-O-acetyl-D-glucal (25.0 g) and lithium bromide hydrate (25.0 g) in acetonitrile (750 ml), activated resin prepared as in Example 1 (25.0 g) and water (30 ml) were added and stirred at room temperature for 4 h. The product was isolated as described for Example 1. Crystallization from ethyl acetate-hexane gave the title compound as colorless crystals (17.8 g). [α]D20 =+71.2°±2° (c 1.06, CHCl3). 1H NMR δ: 5.40 (broad s, H-1α), 5.35 (m, H-3α), 4.9-5.05 (H-4α,β, H-3β, H-1β), 4.18-4.28 (H-6a, H-5α), 4.10 (H-6bβ), 4.06 (H-6bα). 3.65 (m, H-5β), 2.38 (m, H-2eqb), 2.25 (H-2eqα), 1 79 (H-2axα), 1.67 (H-2axβ). MS m/e 273.11 (M-H2O), 213.10, 153.07.

Workup

  1. additionwere added
  2. customThe product was isolated
  3. customCrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-af4e337f3fd549b7994a74fa280dbead
Source dataset
uspto-grants-1992_07
Patent number
US05128463

Reaction notes

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