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Convert D-glucopyranose to 2,3,4- trieth...

Convert `D`-glucopyranose to `2,3,4-` triethyl gluocopynoside.

Text Solution

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First convert `D-`glucose to methyl glucopyranoside with `MeOH//HCl`. Then `overset(6)(C )H_(2)OH` is protected by reacting methyl glucopyranoside with `Ph_(3)C-Cl` (trityl chloride).

only `overset(6)(C )H_(2)OH` is etherified giving `overset(6)(C )H_(2)OCPh_(3)` group. the `2^(@)OH` group. are sterically hindered and do not react with the bulkyl `(Ph_(3)C-Cl)` group.
The free `OH` groups of tritylated methyl glucosides are now methylated with `Me_(2)SO_(4)//NaOH` followed by acidic hydrolysis removes both trityl group and the glycosidic Me group leaving `OMe` group at `C^(2),C^(3)`. and `C^(4)` intact. The hydrolysis of `-OCPh_(3)`, group proceeds by the formation of stable `Ph_(3)C^(o+)` (triphenyl methyl carbocation).
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Knowledge Check

  • beta-D-(+) Glucopyranose is

    A
    Cylic structure of glucose
    B
    It is dextrorotatory because 'D' is placed before name of it
    C
    it is anomer of `alpha-D-(+)` Glucosepyranose
    D
    Pyranose naming is due to it's anlogy with pyrane

  • alpha -D-glucopyranose and beta -D-glucopyranose are :

    A
    stereosiomers
    B
    diastereoisomers
    C
    enentiomers
    D
    anomers

  • alpha-D- Glucopyranose and beta-D- glucopyranose are

    A
    diastereomers
    B
    epimers
    C
    anomers
    D
    all of these

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