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O
O
OH
O
O
O
TMSCl
base
AcO
AcO
AcO
O
O
OSiMe
3
Ph
Ph
Ph
O
N
O
NaIO
4
HN
O
NH
H
N
AcO
AcO
Ph
Scheme 18
D-
glycero
-D-
manno
-heptose
Lubineau reaction
AcO
HO
AcO
AcO
1. Ac
2
O
2. Na BH
4
OAc
HO
OH
Ac O
O
A
c
O
Ac O
O
O
AcO
HO
AcO
HO
Ac O
OR
O
P
O
R=CH
2
CH
2
CN
Ad = adenine
O
OH
OAd
Scheme 19
Long chain C-glycosyl ketohydrazones were prepared as new sur-
factants from fatty acid hydrazides and C-glycosyl methyl ketones.
104
Using a one-pot Friedl¨nder reaction, different sugar-based heterocyclic
derivatives were synthesized from their corresponding b-C-glycosyl ke-
tones arising from protected, partially protected or unprotected carbo-
hydrates.
105
These new scaffolds were tested for their antibacterial
activities. Acetylated methyl ketones could undergo a double Friedel
Crafts reaction with pyrrole followed by an acid catalysed MacDonald
(2
þ
2) reaction with acetone, giving access to calix[4]pyrroles with
carbohydrates moieties.
106
5 Conclusion
We have described herein some seminal scientific breakthroughs of
Professor Lubineau, concerning water-promoted reactions such as
cycloadditions, N-glycosylations and C-glycosyl compound formation,
with a focus on new synthons. According to the principles of green
chemistry, they can be considered as green synthons. Due to their ac-
cessibility, they were largely used in many syntheses and in various fields.
References
1
(a) S. David, A. Lubineau and J.-M. Vat`le, J. Chem. Soc. Perkin Trans 1, 1976,
1831; and (b) S. David and A. Lubineau, New. J. Chem., 1977, 1, 375.
2
(a) A. Lubineau, J. Aug´ and Y. Queneau, Synthesis, 1994, 741; and (b) A.
Lubineau and J. Aug´, Top. Curr. Chem., 1999, 206,1.
3
(a) F. Garcia Calvo-Flores, ChemSusChem, 2009, 2, 905; and (b) P. Anastas
and N. Eghbali, Chem. Soc. Rev., 2010, 39, 301.
4
(a) J. Aug´, Green Chem., 2008, 10, 225; and (b) J. Aug´ and M.-C.
Scherrmann, New J. Chem., 2012, 36, 1091.
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