Expeditious route to F unit building block of moenomycin A

Synthesis of the versatile F sugar unit building block of moenomycin A, Phenyl 2-O-levulinoyl-4-C-methyl-1-thio-β-D-glucopyranosiduronic acid is described starting from phenyl 1-thio-β-D-galactopyranoside. The key synthetic steps included: (I) Regioselective protection of the 3-OH group of phenyl 6-...

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Bibliographic Details
Published in:Tetrahedron letters 1999, Vol.40 (1), p.5-8
Main Authors: Kakarla, Ramesh, Ghosh, Manuka, Anderson, Jan A., Dulina, Richard G., Sofia, Michael J.
Format: Article
Language:English
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Summary:Synthesis of the versatile F sugar unit building block of moenomycin A, Phenyl 2-O-levulinoyl-4-C-methyl-1-thio-β-D-glucopyranosiduronic acid is described starting from phenyl 1-thio-β-D-galactopyranoside. The key synthetic steps included: (I) Regioselective protection of the 3-OH group of phenyl 6-O-trityl-1-thio-β-D-galactopyranoside as its TBDMS ether, (ii) TBAF mediated TBDMS group migration from the C-3 to C-2 position of phenyl 3-O-TBDMS-4-C-methyl-6-O-trityl-1-thio-β-D-galactopyranoside, and (iii) Selective deprotection of TBDMS and trityl groups in phenyl 2-O-levulinoyl-3-O-TBDMS-4-C-methyl-6-O-trityl-1-thio-β-D-glucopyranoside by DDQ. [Display omitted]
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)80003-8