Expeditious route to F unit building block of moenomycin A

✍ Scribed by Ramesh Kakarla; Manuka Ghosh; Jan A. Anderson; Richard G. Dulina; Michael J. Sofia

• Book ID: 104260650
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 242 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)80003-8

✦ Synopsis

Synthesis of the versatile F sugar unit building block of moenomycin A, Phenyl 2-O-levulinoyl-4-C-methyl-l-thio-13-D-glucopyranosiduronic acid is described starting from phenyl l-thio-13-Dgalactopyranoside. The key synthetic steps included: (I) Regioselective protection of the 3-OH group of phenyl 6-O-trityl-l-thio-13-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-l-thio-13-Dgalactopyranoside, and (iii) Selective deprotection of TBDMS and trityl groups in phenyl 2-O-levulinoyl-3-O-TBDMS-4-C-methyl-6-O-trityl-l-thio-13-D-glucopyranoside by DDQ.