135253-58-6Relevant academic research and scientific papers
3 - deoxy - D - monno -2 - octanone method for synthesizing sugar acid ammonium salt
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Paragraph 0057-0058, (2017/01/02)
The invention relates to a synthetic method of 3-deoxidized-D-sweet dew-2-octulosonic ammonium salt. The synthetic method comprises the following steps: using D-sweet dew as a raw material and performing the reaction on D-sweet dew and 2,2-dimethoxy propane; protecting hydroxy at 2 and 3 positions and 5 and 6 positions by isopropylidene to obtain an intermediate in a formula I; performing the reaction on a product in the formula I and 2-dimethoxy phosphoroso-2-dimethyl tertiary butyl silica ethyl acetate in a formula II to obtain an intermediate in a formula III; removing a silicyl oxide protecting group in a product in the formula III to form intramolecular hemiketal so as to obtain an intermediate in a formula IV; performing the deprotection, saponification and ammonium salt formation reaction on a product in the formula IV to obtain the final product 3-deoxidized-D-sweet dew-2-octulosonic ammonium salt. The method has the advantages of low price of the raw material, easiness for obtaining the raw material, mild reaction condition, simplicity and convenience for operation, high safety, high route total yield, simplicity for purification treatment on the final product and stable quality of the final product, and thus, the synthetic method disclosed by the invention enables the total cost to be greatly reduced and is suitable for the requirements on large-scale industrial production.
Efficient Large Scale Syntheses of 3-Deoxy- d -manno-2-octulosonic acid (Kdo) and Its Derivatives
Feng, Yingle,Dong, Jie,Xu, Fangyuan,Liu, Aiyun,Wang, Li,Zhang, Qi,Chai, Yonghai
supporting information, p. 2388 - 2391 (2015/05/27)
An efficient method to rapidly synthesize 3-deoxy-d-manno-2-octulosonic acid (Kdo) and its derivatives in large scale has been developed. Starting from d-mannose, the di-O-isopropylidene derivative of Kdo ethyl ester was prepared in three steps on a scale of more than 40 g in one batch in an overall yield of 75-80% without any intermediate purification. Kdo, Kdo glycal, and 2-acetylated Kdo ester were synthesized quickly in high yield from a di-O-isopropylidene derivative of Kdo ethyl ester. 2-Deoxy-β-Kdo ester was obtained with high stereoselectivity via the epimerization of the α-isomer using t-BuOH as a proton source.
Syntheses of 2-keto-3-deoxy-D-xylonate and 2-keto-3-deoxy-L-arabinonate as stereochemical probes for demonstrating the metabolic promiscuity of sulfolobus solfataricus towards D-xylose and L-arabinose
Archer, Robert M.,Royer, Sylvain F.,Mahy, William,Winn, Caroline L.,Danson, Michael J.,Bull, Steven D.
supporting information, p. 2895 - 2902 (2013/03/28)
Practical syntheses of 2-keto-3-deoxy-D-xylonate (D-KDX) and 2-keto-3-deoxy-L-arabinonate (L-KDA) that rely on reaction of the anion of ethyl 2-[(tert-butyldimethylsilyl)oxy]-2-(dimethoxy phosphoryl) acetate with enantiopure glyceraldehyde acetonide, followed by global deprotection of the resultant O-silyl-enol esters, have been developed. This has enabled us to confirm that a 2-keto-3-deoxy-D-gluconate aldolase from the archaeon Sulfolobus solfataricus demonstrates good activity for catalysis of the retro-aldol cleavage of both these enantiomers to afford pyruvate and glycolaldehyde. The stereochemical promiscuity of this aldolase towards these enantiomeric aldol substrates confirms that this organism employs a metabolically promiscuous pathway to catabolise the C5-sugars D-xylose and L-arabinose.
Base-catalyzed direct aldolization of α-alkyl-α-hydroxy trialkyl phosphonoacetates
Corbett, Michael T.,Uraguchi, Daisuke,Ooi, Takashi,Johnson, Jeffrey S.
supporting information; experimental part, p. 4685 - 4689 (2012/06/18)
Pass the P: Catalytic direct aldol addition of α-hydroxy trialkyl phosphonacetates to aldehydes affords α-hydroxy-β-phosphonyloxy ester products (see scheme). The fully substituted glycolate enolate intermediate is generated in situ under mild conditions by a [1,2] phosphonate-phosphate rearrangement. High enantioselectivity and dramatic enhancement of reaction diastereocontrol is realized by the application of chiral iminophosphorane catalysts. Copyright
