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β-Oxy-α-diazo-carbonyl compounds. Part 5: An improved synthesis of β-hydroxy-α-diazo esters derived from monosaccharides and synthetic applications in the chemistry of 3-deoxy-2-ulosonic acids

✍ Scribed by Francisco Sarabia; Fidel Jorge López-Herrera

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
79 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

Reactions of ethyl 2-diazoacetate with aldehydo sugars and monosaccharide derivatives in their hemiacetal form are reported. The use of diethyl zinc led to an improvement of yields and shorter reaction times compared with neutral conditions as previously described. The resulting products represent potentially useful substrates for the synthesis of 3-deoxy-2-keto-ulosonic acid derivatives. Thus, diazo derivatives from D-mannose were transformed into Ko and 3-epimer Ko derivatives in a straightforward process by reaction with mCPBA.

📜 SIMILAR VOLUMES

ChemInform Abstract: β-Oxy-α-diazo-carbo
ChemInform Abstract: β-Oxy-α-diazo-carbonyl Compounds. Part 6. Synthesis and Reactivity of 3-Deoxy-2-diazo-esters Derived from Monosaccharides. Applications in the Synthesis of 2-C-Alkyl-KDO Analogues and Related Compounds.
✍ Francisco Sarabia; Fidel Jorge Lopez-Herrera 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 40 KB 👁 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

β-Oxy-α-diazo carbonyl compounds. III. R
β-Oxy-α-diazo carbonyl compounds. III. Rh2(AcO)4 mediated decomposition of β-acetoxy-α-diazo esters. Application to the synthesis of natural 3-deoxy-2-keto aldonic acids (KDO and DAH)
✍ Fidel J. López-Herrera; Francisco Sarabia-García 📂 Article 📅 1994 🏛 Elsevier Science 🌐 French ⚖ 322 KB

p-Acemxy-a4iaz.o esters yield a-en01 amate esters quantitatively by reaction with dirhodittm temmtate. The reaction was used to prepare tJte major natural cmtpounds 3-Deoxy-D-arabiio-2-Heptulosonic lrcid (DAH, 1) aud 3-Deoxy-D-manno-2-Cktulo.wnic