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The chemistry of cellobiose and lactose part 7 selective benzoylation of methyl beta lactoside

Bhatt, R.S.; Hough, L.; Richardson, A.C.

Journal of the Chemical Society Perkin Transactions I 18: 2001-2005

1977

Accession: 006613867
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The selective benzoylation of methyl .beta.-lactoside with various proportions of benzoyl chloride in pyridine was studied. The 3',6'-dibenzoate, the 3',6,6'-tribenzoate, the 2,3',6,6'-tetrabenzoate and the 2,2',3',4',6,6'-hexabenzoate have each been isolated, in yields of between 21-31%. The 2,3',4',6,6'- and 2,2',3',6,6'-pentabenzoates were also encountered, but in much lower yields. The order of reactions of the 7 hydroxy-groups in methyl .beta.-lactoside is probably 6' > 3' > 6 > 2 > 2' > 4' > 3.

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Related References

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