Water → GlyTouCan:G77954UO

HRID 653759Notes

Reaction equation

HRID 653759 reaction equation
[CH3:1][C@@H:2]1[O:7][CH:6]=[CH:5][C@H:4]([O:8]C(C)=O)[C@@H:3]1[O:12]C(C)=O.[OH2:16].[Br-].[Li+].O>C(#N)C>[OH:16][CH:6]1[O:7][C@@H:2]([CH3:1])[C@@H:3]([OH:12])[C@@H:4]([OH:8])[CH2:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 688127AC1Lele9HCID 23702478Lithium bromide hydrate

Product 1

HCID 11804916GlyTouCan:G77954UOYield 115.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3,4-di-O-acetyl-L-fucal (5.0 g) and lithium bromide hydrate (5.0 g) in acetonitrile (150 ml), activated resin prepared as in Example 1 (3.0 g) and water (6 ml) were added and stirred at room temperature for 15 min. The product was isolated as described for Example 1. Purification by chromatography on a column of Silica Gel using ethyl acetate-hexane (3:8) as eluant gave the title compound (4.0 g). α:β=9:4. [α]D20 =-57.6°±2°(c 1.03, CHCl3). 1H NMR δ: 5.45 (d, H-1α), 5.35 (m H-3α), 5.19 (H-4α), 5.10 (d, H-4β), 4.98 (m, H-3β), 4.87 (dd, H-1β), 4.33 (H-5α), 3.73 (m, H-5β), 2.04 & 1.86 (m, H-2). MS (calc. mass=232). Obs. m/e 231.13, 215.12, 155.09 (100%).

Workup

  1. additionwere added
  2. customThe product was isolated
  3. customPurification by chromatography on a column of Silica Gel

Sources & evidence

ORD record
ord-bf31d1e24b0a49629751aa8cba0a0f33
Source dataset
uspto-grants-1992_07
Patent number
US05128463

Reaction notes

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