2-Methyl-(1,2-dideoxy-a-D-glucopyrano)-[2,1-d]-2-oxazoline synthesis

3synthesis methods

Product Name:2-Methyl-(1,2-dideoxy-a-D-glucopyrano)-[2,1-d]-2-oxazoline
CAS Number:22854-00-8
Molecular formula:C8H13NO5
Molecular Weight:203.19

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2-Methyl-(1,2-dideoxy-a-D-glucopyrano)-[2,1-d]-2-oxazoline

22854-00-8
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Yield:22854-00-8 52.9%

Reaction Conditions:

with 2-chloro-1,3-dimethyl-1H-benzimidazole-3-ium chloride;triethylamine in water at 0 - 4; for 0.5 h;

Steps:

2 Synthesis Example 2 (Synthesis of GNO)

N-acetylglucosamine (GlcNAc, manufactured by Sigma-Aldrich) (22.0 mg, 100 μmol)Was added 0.5 M CDMBI aqueous solution (600 μL) and the mixture was stirred.Triethylamine (104.5 μL, 749.9 μmol) was added at 0 ° C. and shaken at 4 ° C. and 1000 rpm for 30 minutes.The obtained reaction solution was subjected to reverse phase HPLC under the following conditions, separation and purification was carried out, 0.1 N sodium hydroxide (100 μL) was added and freeze-dried,To obtain N-acetylglucooxalide (GNO: 11.7 mg, yield 52.9%) represented by the following structural formula (h).

References:

JP2018/21001,2018,A Location in patent:Paragraph 0093; 0094

Benzenesulfonic acid, 4-methyl-, 2-[2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]hydrazide

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References

β-D-Glucopyranose, 2-amino-2-deoxy-, hydrochloride (1:1)

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References