Ethyl Acetate → HCID 70132709, compound

HRID 1769239Notes

Reaction equation

HRID 1769239 reaction equation
C([O:4][C@H:5]1[O:10][C@H:9]([CH2:11][O:12][C:13](=[O:15])[CH3:14])[CH:8]=[C:7]([Br:16])[C:6]1=[O:17])(=O)C.BrC1C(=O)[C@@H]2OC[C@H](C=1)O2.O.[OH-].[Li+].C(OCC)(=O)C>O1CCCC1.O>[C:13]([O:12][CH2:11][C@H:9]1[O:10][CH:5]([OH:4])[C:6](=[O:17])[C:7]([Br:16])=[CH:8]1)(=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 11458381HCID 11458381, compoundHCID 70131092HCID 70131092, compound

Product 1

HCID 70132709HCID 70132709, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

200 mg of 1,6-di-O-acetyl-3-bromo-3,4-dideoxy-α-D-glycero-hex-3-enopyranos-2-ulose prepared in the same manner as in the above Intermediate Preparation Example 4 from 1,6-anhydro-3-bromo-3,4-dideoxy-β-D-glycero-hex-3-enopyranos-2-ulose (Intermediate No. 4) prepared by the method disclosed in Carbohydrate Research (1981), Vol. 93, 284-287, was dissolved in 6 ml of tetrahydrofuran-water (5:1), and 70 mg of lithium hydroxide monohydrate was added thereto. The mixture was stirred at room temperature for 30 minutes. To the reaction solution, 100 ml of ethyl acetate was added. The mixture was washed three times with 100 ml of a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained syrup crude product was purified by thin layer chromatography for separation (NO-5744, manufactured by Merck, ethyl acetate: hexane=1:1) to obtain 40 mg of the desired product (Intermediate No. 18) as a slightly yellow liquid. The NMR analytical data of this product are as follows.

Workup

  1. customprepared by the method
  2. washThe mixture was washed three times with 100 ml of a saturated sodium chloride aqueous solution
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained syrup crude product was purified by thin layer chromatography for separation (NO-5744, manufactured by Merck, ethyl acetate: hexane=1:1)

Sources & evidence

ORD record
ord-6d5f12a3a12e4533928366aa47464a4c
Source dataset
uspto-grants-1995_01
Patent number
US05380834

Reaction notes

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