ChemInform Abstract: SYNTHESIS OF MACROLIDE ANTIBIOTICS PART 1, STEREOSPECIFIC ADDITION OF METHYLLITHIUM AND METHYLMAGNESIUM IODIDE TO METHYL ALPHA‐D‐XYLO‐HEXOPYRANOSID‐4‐ULOSE DERIVATIVES, DETERMINATION OF THE CONFIGURATION AT THE BRANCHING CARBON ATOM BY CARBON‐13 NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY

Miljković, Momčilo; Gligorijevic, Miodrag; Satoh, Toshifumi; Miljković, D.

doi:10.1002/chin.197439461

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1982

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“…Therefore, these reactions of 4 and 5 were examined at first. As shown in Table I, reaction of 4 with methyllithium at -78°C in ether gave exclusively the axial attack product (7), while that with methylmagnesium iodide in ether at -78°C gave only the equatorial attack product (8). The Grignard reaction in ether-tetrahydrofuran (I : I) under reflux gave 7 and 8 in the ratio of I to I.…”

Section: Resultsmentioning

confidence: 98%

Branched-chain Sugars. XXIX. Synthesis of Moenuronic Acid (4-C-Methyl-d-glucuronic Acid)

Sato¹,

Kubo²,

Nie³

et al. 1982

Bulletin of the Chemical Society of Japan

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Moenuronic acid (4-C-methyl-d-glucuronic acid), a branched-chain sugar component of moenomycin A, was synthesized by the introduction of an axial C-methyl group into methyl 2,3-di-O-benzyl-6-O-trityl-α-d-xylo-hexopyranosid-4-ulose by the reaction with methyllithium, followed by deprotection and platinum-catalyzed oxidation of the C-6 position. Stereoselectivities in a few reactions for the introduction of C-methyl group were examined.

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Section: Resultsmentioning

confidence: 98%