Glucose Wittig reaction with

A 3-deoxy-3-C-methyl-D-glucose derivative has been used to prepare the 5-ulose (55) by conventional steps, and this was then transformed to 3,5-dideoxy-3,5-di-C-methyl-L-idose derivatives (56) and (57) via Wittig reaction with methylene triphenylphosphorane. ... 

The 3-fluoro-3-C-ethoxydicarbonyl-D-glucose derivative (44) yielded the branched-chain compounds (45) and (46) in a Wittig reaction (Scheme 11) the cij-isomer of (46), required for the synthesis of showdomycin analogues, was not formed, presumably for steric reasons some product (47) with the... 

The asymmetric aspects of the syntheses of 169 and 170 appear in the workbook. The other three alkenes were made by E-selective Wittigs with stabilised ylids or HWE reactions. The sulfone 172 for the Julia reaction was prepared from 171, in turn prepared from glucose and gave the corresponding E-alkene (a modified version of 168) in excellent yield and perfect E-selectivity. 

Wittig olefin 104 formed in a reaction of the ylide 91 and a protected D-glucose aldehyde 103 was transformed to the lactone 106 under hydrogenation and subsequent cyclization. In the next step an oxo-function at the a position was introduced via cxo-enamine system, followed by photooxidation. Final deprotection of 108, then treatment with ammonia afforded D-gluco-KDO ammonium salt 109. 

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