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epothilone d production

Deprotection of the C3 and C7 silyl ethers was carried out using HF?pyr, providing epothilone D. The equation of epothilone d production is below.
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    properties of epothilone d

     

    Chemical Formula: C27H41NO5
    Molecular Weight: 491.68
    Elemental Analysis: C, 65.95; H, 8.40; N, 2.85; O, 16.27; S, 6.52
    Appearance: White of off-white crystal
    Assay: 95.0%min;98%
    Chemical structure:

     

    epothilone d production

     

    The lithium enolate of ethyl ketone 7 was generated by exposure to LDA at -78 °C. Addition of aldehyde 10b provided the desired syn, anti-aldol adduct as the major product in 83% yield and 8:1. After protection of the C7 hydroxyl as a TBS ether, the primary alcohol was liberated by exposure to acidic methanol solution. The C1-carboxylic acid was generated by two-step oxidation in 90% yield. Subsequent selective removal of the C15 TBS ether was then accomplished with TBAF. Macrolactonization proceeded efficiently using the Yamaguchi method13 to provide the 16-membered lactone in 77% yield. Deprotection of the C3 and C7 silyl ethers was carried out using HF‚pyr, providing epothilone D. The equation of epothilone d production is below:

     

     

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