Method for preparing hexose derivatives

Details Method for preparing hexose derivatives Method for preparing hexose derivatives

2011-07-26

2011-07-26

Jiang, Shaojia Anna (Department: 1623)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

C536S004100, C536S120000

Reexamination Certificate

active

07985856

ABSTRACT:
A method for preparing hexose derivatives comprises the steps of providing a silylated hexose, treating the silylated hexose with a first carbonyl compound in the presence of a catalyst to form an ketalized hexose, treating the ketalized hexose with a second carbonyl compound followed by treating with a first reductant to form an etherized hexose, and converting the etherized hexose into a target hexose derivative, which can be 2-alcohol hexose, 3-alcohol hexose, 4-alcohol hexose, or a 6-alcohol hexose. In particular, the present invention can prepare the hexose derivatives with highly regioselective scheme to protect individual hydroxyls of monosaccharide units and install an orthogonal protecting group pattern in a one-pot manner.

REFERENCES:
patent: 3829413 (1974-08-01), Deslongchamps
patent: 3856843 (1974-12-01), Nagai et al.
patent: 5344924 (1994-09-01), Arora
Liptak et al (Trimethylsilyl Triflate—Catalysed Acetal Formation Between Silylated Hexopyranosides and Methyl Pyruvate, J. Carbohydrate Chemistry, 8(4), 629-644 (1989).
Document cited in Taiwanese search report dated Aug. 3, 2010 of the Taiwanese counterpart application.

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