MindMap Gallery chemical synthesis of sugar
This is a mind map about the chemical synthesis of sugars, including glycosidation reactions, sugar synthesis strategies, Solid-phase synthesis of oligosaccharides, protection of sugars, etc.
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chemical synthesis of sugar
Conformations of common monosaccharides
sugar protection
Stereoselectivity
regional selectivity
protecting group
Temporary protective base
Keep protecting group
Classification
hydroxyl protecting group
Ester protecting group
acetate
Parabens
Haloacetates
trifluoroacetyl
Pentafluoroacetyl
Chloroacetyl
Bromoacetyl
Sulfonate ester
methanesulfonyl
trifluoromethanesulfonyl
p-toluenesulfonyl
Selective deacetylation of terminal centers
Ether protecting group
Benzyl ether
Benzene bromide, sodium alcohol, DMF
Trichloroacetimidate benzyl ester, trifluoromethanesulfonic acid
Benzene bromide, silver oxide, DMF
Palladium catalyzed hydrogenolysis
p-methoxybenzyl ether
DDQ, dichloromethane/water
Allyl ether
Propylene bromide, barium oxide
Allyl trichloroacetimide, TfOH trifluoromethanesulfonate
Silane ether
Chlorinated trialkylsilane and alcohol in alkaline catalyst
Acetal and ketal protecting groups
One carbonyl group and two hydroxyl groups are condensed under acid catalysis to obtain acetal
regional selectivity
Lithium aluminum tetrahydride, aluminum chloride
hydroxyl group at position 6
Sodium cyanoborohydride, hydrochloric acid/diethyl ether
hydroxyl group at position 4
NBS
6 bromine
selective protection
The reactivity of the primary hydroxyl group is greater than that of the secondary hydroxyl group
The secondary hydroxyl group of the equatorial bond is more reactive than the secondary hydroxyl group of the upright bond.
The ether bond of trialkyl tin can change the relative activity of the hydroxyl group of the equatorial bond.
terminal protecting group
Keep protecting group
Ether group
Temporary protective base
Allyl
selenophenyl
Glucoside
alkenyl
Amino protecting group
Azide group
nucleophilic substitution
alkenose addition
reduction
Amide protecting group
Phthalyl
Alkaline condition treatment
Trichloroethoxycarbonyl
Acidic condition treatment
Carboxyl protecting group
Benzyl ester
Alkali treatment
Methyl ester
Alkali treatment
choose
Cheap, easy to obtain, stable and non-toxic
No chiral centers are introduced
process stable
Easy to insert and remove
Easy to separate from product
Glycosylation reaction
effect
End group effect
definition
In the chair conformation, each substituent is energetically more favorable in the horizontal bond position than in the vertical bond position, but the end groups are opposite.
neighbor participation effect
Ester protective groups or amide protective groups attack carbocation through carbonyl oxygen to form acyloxynium ion intermediates.
trichloroacetamido
remote participation effect
electronic effect
When the ortho-position of the hydroxyl group of the glycosyl acceptor is an electron-withdrawing group, the electronegativity of the hydroxyl oxygen decreases and the nucleophilicity decreases.
solvent effect
Ether
Acetonitrile
1,4 dioxane
Glycosylation method
Glycosyl donor
Trichloroacetimide ester
Glycosyl imide ester
Trichloroacetimide ester of sugar
preparation
1 Hydroxy compound and trichloroacetonitrile, alkaline
catalyst
Boron trifluoride etherate complex, trimethylsilyl trifluoromethanesulfonate
trifluoroacetimide ester of sugar
preparation
1 Hydroxy compound and trifluoroacetylphenylimine chloride
Trifluoroacetylphenylimine chloride
Trifluoroacetic acid primary ammonia, triphenylphosphine-triethylamine-carbon tetrachloride
Thioglycosides
halosugar
Pentenyl glycoside
Succinimidyl bromide and iodonium dicloridine perchlorate
oGlycoside
Zinc Oxide Phenol Heating α
p-Toluenesulfonic acid low temperature beta
Sugar synthesis strategy
sugar chain elongation direction
Non-reducing end glycosylation reaction
Donor and acceptor coupling, region selection deprotection, newly generated oligosaccharide becomes new acceptor
Glycosylation reaction at reducing end
The donor and acceptor are coupled and the resulting oligosaccharide is converted into a glycosyl donor
How sugar chains are assembled
Linear Oligosaccharide Synthesis Strategies
Convergent Oligosaccharide Synthesis
fragment assembly
Bidirectional oligosaccharide synthesis
Sugar chain synthesis continuity
Stepwise glycosylation
continuous glycosylation
Preactivation method
independent of donor activity
Donor-hidden-activated glycosylation strategy
Before the sugar donor is activated, it is in a reversible inactivation state and used as an acceptor for glycosylation reaction. After being converted into an activatable leaving group, it is further used for the glycosylation reaction of the sugar donor.
o(p-Methoxyphenylethynyl)phenyl
o-iodophenyl glycoside
o-Isopropylthiobenzyl
o-isopropyl sulfoxide benzyl oxyglycoside
s-O-isopropylthiobenzylthio
o-isopropyl sulfoxide benzyl thioglycoside
sugar donor reactivity
The use of different protective groups on the sugar rings of the two sugar structures causes the two to have different activation states of the catalyst to achieve selective glycosylation reactions.
Relative reactivity value: Taking the sugar donor reactivity of peracetylmannose to glucosinolate as the reference value
Orthogonal activated glycosylation
Use different leaving groups and activate different donors using orthogonal conditions
Solid phase synthesis of oligosaccharides
The key issue
Choice of synthesis strategy, reducing end or non-reducing end connected to carrier
Selection of polymers and linkers that are stable during synthesis and easy to break from the support when needed
Protecting group selection
Efficient and selective glycosylation
Analysis of sugars on a carrier
Strategy
Glycosyl Donor Linking Carrier
Glycosyl receptor linker
Block by-product cap-tag
Blocking reagents react with glycosylated hydroxyl groups
Stable with hydroxyl linkage
Does not interact with protecting groups, requires different labels
Easy to separate
polymer carrier
merrifield resin (polystyrene, containing divinylbenzene)
tentagel
Polyethylene glycol to polystyrene
connecting arm
Silicon ethers
acids and bases
glucosinolates
Oxidative fracture
hydrogenation fracture
photofragmentation
Alkene displacement cleavage
protecting group
Keep protecting group
Benzyl ether
Temporary protective base
acyl
Silicon ether
Donor