Stereoselective AromaticO-Glycosylation of Glycosyl Chloride with Arylboronic Acid under an Air Atmosphere
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(15), С. 10721 - 10734
Опубликована: Июль 24, 2023
A
novel
exclusive
β-selective
O-aryl
glycosylation
was
developed
using
glycosyl
chloride
and
arylboronic
acid
with
a
palladium
catalyst
under
an
air
atmosphere.
The
reaction
insensitive
to
moisture
characterized
readily
available
bench-stable
as
substrates.
diverse
range
of
substrate
scopes,
including
various
acids
donors,
well-tolerated
in
this
method.
Arylboronic
oxidized
by
O2
produce
phenol
the
aromatic
source.
This
new
strategy
provides
alternative
route
may
find
broad
applications
efficient
synthesis
bioactive
glycosides
future.
Язык: Английский
Insertion of Glycosylidene Carbenes into Phenolic O–H Bonds for the Synthesis of O-Aryl Glycosides
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 18, 2025
We
present
a
new
strategy
for
the
synthesis
of
O-aryl
glycosides
through
formal
insertion
glycosylidene
carbenes
into
O–H
bond
phenols.
The
key
carbene
intermediates
were
generated
in
situ
by
copper-catalyzed
oxidation
bench-stable
diaziridine
precursors.
This
method
enables
glycosylation
variety
phenols
with
good
yields,
excellent
diastereoselectivity,
and
chemoselectivity,
providing
highly
practical
late-stage
complex
natural
products
bioactive
agents.
Язык: Английский
Studies Concerned with the Structure and Synthesis of the Anti‐viral Tropolone Glycoside Liriosmaside A
ChemistryOpen,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 8, 2025
Abstract
A
bromotropone
corresponding
to
the
agylcone
of
glycosylated
sesquiterpenoid
natural
product
liriosmaside
has
been
prepared
over
ten
steps
and
in
a
fully
regio‐controlled
manner
through
gem
‐dibromocyclopropane‐mediated
ring‐expansion
readily
accessible
decalenone.
Pd[0]‐mediated
glucosylation
reaction
applied
this
afforded
mixture
from
which
an
enantiomerically
pure
cross‐coupling
could
be
obtained
its
structure
confirmed
single‐crystal
X‐ray
analysis
derivative.
Various
(unsuccessful)
attempts
are
described
selectively
acylate
last
compound
thereby
install
3‐hydroxy‐3‐methylglutaric
acid
or
HMGA‐containing
side
chain
title
product.
literature
survey
other
products
embodying
HMGA
motif
suggest
that
co‐metabolite
B
S
‐configured
at
C3”.
The
evaluation
glucosylated
tropone
series
anti‐bacterial,
anti‐fungal
cytotoxicity
assays
reveals
it
is
inactive
all
these
so
emphasizing
prospect
related
troponoids,
including
B,
can
serve
as
useful
models
for
new
anti‐viral
agents.
Язык: Английский
Total Syntheses of the Tropolone-Containing Sesquiterpene Olaximbriside A and Its Decarbonylated Counterpart Olaximbriside B
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 12, 2024
The
racemic
modification
of
the
α-tropolone-containing
sesquiterpene
olaximbriside
A
[viz.
(±)-
Язык: Английский
Mechanistic Investigation of the Pseudo-Halogen Effect in Enantioselective Aminocatalyzed [6 + 4] and [10 + 6] Cycloadditions: Enabling Unique Favorskii-Like Rearrangements
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 28, 2024
A
mechanistic
investigation
into
the
novel
combination
of
Язык: Английский
Synthesis of propargyl glycosides of Streptococcus pneumoniae serotypes 6A and 6B for glycoconjugate vaccines
Tianyao Meng,
Brady Davis James,
Jared Haymore
и другие.
Tetrahedron,
Год журнала:
2024,
Номер
165, С. 134186 - 134186
Опубликована: Авг. 8, 2024
Язык: Английский
Highly Regioselective Dehydrogenative Hydrazination of Tropones
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 15, 2024
Direct
C(sp
Язык: Английский
Stereoselective Conversions of Carbohydrate Anomeric Hydroxyl Group in Basic and Neutral Conditions
Molecules,
Год журнала:
2024,
Номер
30(1), С. 120 - 120
Опубликована: Дек. 31, 2024
The
rapidly
growing
glycoscience
has
boosted
the
research
on
synthesis
of
glycans
and
their
conjugates,
which
are
centered
stereoselective
formation
glycosidic
bonds.
Compared
to
mainstream
acid-promoted
glycosylation
method
that
undergoes
S
Язык: Английский