Switchable and Stereospecific C-Glycosylation Strategy via Formal Functional Group Deletion
Xiaoshen Ma,
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Stephen J. Sujansky
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The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 9, 2025
Carbohydrates
constitute
an
important
class
of
biologically
relevant
natural
products.
Among
the
synthetic
glycomimetics,
C-glycosides
are
particularly
interesting
due
to
their
chemical
and
metabolic
stability
toward
acidic
enzymatic
hydrolysis
at
anomeric
position.
The
stereochemical
outcomes
traditional
methodologies
access
rely
heavily
on
substrate
control.
Herein,
we
report
a
novel
strategy
diverse
with
precise
control
position
via
formal
functional
group
deletion,
where
both
α-
β-anomers
furanoses
pyranoses
can
be
obtained
as
single
stereoisomers.
Additionally,
broad
scope
heterocyclic
this
further
illustrates
its
potential
for
empowering
future
application
in
biology
research
drug
discovery.
Language: Английский
Radical dehydroxylative C-glycosylation of 1-hydroxycarbohydrates enabled by photoredox catalysis
Wenyan Shi,
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Xingxiu Yan,
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Wuyin Wang
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et al.
Green Synthesis and Catalysis,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 1, 2025
Language: Английский
Stereoselective synthesis of C-glycosides from glycals and organotrifluoroborate salts
Karwan Abdulmajed Othman,
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Yimin Xiang,
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Yue Wang
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et al.
Chemical Communications,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 1, 2025
Harnessing
aryltrifluoroborates'
stability
and
reactivity,
we
developed
a
Pd-catalyzed
stereoselective
C-glycosylation
under
ambient
conditions,
yielding
diverse
C-aryl
glycosides
with
exclusive
α-stereoselectivity
compatibility
hydroxyl,
amide,
amine
groups.
This
method
enables
functionalization
to
produce
unprotected
C-pyranosides,
2,3-dideoxy
2,3-epoxy
sugars,
late-stage
of
natural
products
drugs.
Language: Английский
ZnI2-Mediated cis-Glycosylations of Various Constrained Glycosyl Donors: Recent Advances in cis-Selective Glycosylations
Molecules,
Journal Year:
2024,
Volume and Issue:
29(19), P. 4710 - 4710
Published: Oct. 4, 2024
An
efficient
and
versatile
glycosylation
methodology
is
crucial
for
the
systematic
synthesis
of
oligosaccharides
glycoconjugates.
A
direct
intermolecular
an
indirect
intramolecular
have
been
developed,
former
can
be
applied
to
medium-to-long-chain
glycans
like
that
nucleotides
peptides.
The
development
a
generally
applicable
approach
stereoselective
construction
glycosidic
bonds
remains
major
challenge,
especially
1,2-
Language: Английский
Creating glycoside diversity through stereoselective carboboration of glycals
Zhenpeng Shen,
No information about this author
Yue Yu,
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Donghai Wu
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et al.
Nature Communications,
Journal Year:
2024,
Volume and Issue:
15(1)
Published: Nov. 23, 2024
Site-specific
modification
of
glycosides
to
enhance
or
alter
the
physiological
properties
parent
molecule
has
become
a
highly
attractive
strategy
in
drug
development.
However,
creating
glycoside
building
blocks
with
multiple
diversifiable
positions
from
readily
available
sugar
precursors
remains
challenging
task.
Herein,
we
present
regio-
and
stereoselective
nickel-catalyzed
carboboration
glycals,
which
offers
platform
for
generating
diversity
diverse
C1
C2
potential.
Specially,
integration
modifiable
boronate
group
at
position
markedly
amplifies
versatility
this
approach,
furnishing
universal
method
swiftly
rare
sugars
C2-site
modifications
through
expedited
downstream
transformations.
This
demonstrates
broad
substrate
scope
tolerates
various
functional
groups
complex
natural
molecular
architectures.
Moreover,
illustrate
synthetic
potential
synthesis
array
analogs
both
products
pharmaceuticals.
Creating
authors
Language: Английский