Condensing agent

Condensing agent refers to an adjuvant which would be added in the condensation reaction. Generally there are catalytic adjuvants and catalytic adjuvants which can combine with the isolated atom or group of atoms generated during the process of condensation. About the former one, there are adjuvants such as the acid catalyst in esterification reaction and aluminum chloride in Friedl-Crafts reaction. And about the latter, there is metallic sodium in Wurtz-Fittig reaction.

A condensation reaction is a chemical reaction in which two molecules or moieties, often functional groups, combine to form a larger molecule, together with the loss of a small molecule like water, ammonia, hydrogen chloride, etc. Sometimes two organic molecules interact to form a larger molecule without emission of simple molecules. This is also known as condensation (reaction), such as aldol condensation.

The selection of condensing agents depends on the type of reaction, structure of the reactant, reaction conditions and the removed substances during the process of the reaction. Protecting groups and condensing agents in chemical synthesis: during chemical synthesis of nucleic acids, both of the nucleoside which plays the role of raw material monomers and the mononucleotide are compounds of polyfunctional group. When they are carrying chemical connections, except the groups of required reaction, other groups would also participate in the reaction, so as to generate by-products of auto-agglutination, misconnection and degradation. This will not only reduce the productivity of synthetic product, but also causes great difficulty in the separation and purification of the product. In order to ensure the phosphate diester bond structure and the nucleotide sequence, it requires a high degree of directionality and specificity in the synthetic reaction. The solution is to use a suitable protecting group and temporarily protect the group which is not required to be involved in the reaction, such as hydroxyl groups on the sugar, amino and hydroxyl phosphate on the base, etc.

Therefore, the selection of protecting groups has a great impact in whether the reaction could success or not. The selection of the condensing agents is important as well. The main reaction in the nucleic acid synthesis reaction is hydroxy reaction between phosphoric acid and RNA or DNA, which could generate phosphate ester linkage. At present, we usually use a kind of condensating agent with high activity and low side effects to react with Phosphate components and form an activated phosphate, and then accomplish the step of components condensation.

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Structure Chemical Name CAS MF
1,1'-Carbonyldiimidazole 1,1'-Carbonyldiimidazole 530-62-1 C7H6N4O
N,N,N',N'-Tetramethyl-O-(N-succinimidyl)uronium hexafluorophosphate N,N,N',N'-Tetramethyl-O-(N-succinimidyl)uronium hexafluorophosphate 265651-18-1 C9H16F6N3O3P
N,N'-Disuccinimidyl carbonate N,N'-Disuccinimidyl carbonate 74124-79-1 C9H8N2O7
1-[(4-Methylphenyl)sulfonyl]-1H-imidazole 1-[(4-Methylphenyl)sulfonyl]-1H-imidazole 2232-08-8 C10H10N2O2S
4,4'-Dimethoxytrityl chloride 4,4'-Dimethoxytrityl chloride 40615-36-9 C21H19ClO2
(3-Hydroxy-3H-1,2,3-triazolo[4,5-b]pyridinato-O)tri-1-pyrrolidinylphosphonium hexafluorophosphate (3-Hydroxy-3H-1,2,3-triazolo[4,5-b]pyridinato-O)tri-1-pyrrolidinylphosphonium hexafluorophosphate 156311-83-0 C17H27F6N7OP2
TOTU TOTU 136849-72-4 C10H17BF4N4O3
4,5-Dicyanoimidazole 4,5-Dicyanoimidazole 1122-28-7 C5H2N4
TSTU TSTU 105832-38-0 C9H16BF4N3O3
DEPBT DEPBT 165534-43-0 C11H14N3O5P
Bis(2-oxo-3-oxazolidinyl)phosphinic chloride Bis(2-oxo-3-oxazolidinyl)phosphinic chloride 68641-49-6 C6H8ClN2O5P
3-Hydroxy-1,2,3-benzotriazin-4(3H)-one 3-Hydroxy-1,2,3-benzotriazin-4(3H)-one 28230-32-2 C7H5N3O2
5-Chloro-1-[bis(dimethylamino)methylene]-1H-benzotriazolium 3-oxide hexafluorophosphate 5-Chloro-1-[bis(dimethylamino)methylene]-1H-benzotriazolium 3-oxide hexafluorophosphate 330645-87-9 C11H15ClF6N5OP
1-Hydroxybenzotriazole hydrate 1-Hydroxybenzotriazole hydrate 123333-53-9 C6H7N3O2
N-Hydroxy-5-norbornene-2,3-dicarboximide N-Hydroxy-5-norbornene-2,3-dicarboximide 21715-90-2 C9H9NO3
1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate 1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate 56602-33-6 C12H22F6N6OP2
N,N,N',N'-Tetramethyl-O-(3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-yl)uronium tetrafluoroborate N,N,N',N'-Tetramethyl-O-(3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-yl)uronium tetrafluoroborate 125700-69-8 C12H16BF4N5O2
6-Chloro-1-hydroxibenzotriazol 6-Chloro-1-hydroxibenzotriazol 26198-19-6 C6H4ClN3O
N-Hydroxysuccinimide N-Hydroxysuccinimide 6066-82-6 C4H5NO3
HDBTU HDBTU 164861-52-3 C12H16F6N5O2P
N-Hydroxyphthalimide N-Hydroxyphthalimide 524-38-9 C8H5NO3
Dipyrrolidino(N-succinimidyloxy)carbenium hexafluorophosphate Dipyrrolidino(N-succinimidyloxy)carbenium hexafluorophosphate 207683-26-9 C13H20F6N3O3P
N,N,N',N'-Tetramethyl-S-(1-oxido-2-pyridyl)thiuronium hexafluorophosphate N,N,N',N'-Tetramethyl-S-(1-oxido-2-pyridyl)thiuronium hexafluorophosphate 212333-72-7 C10H16N3OS.F6P
Bromotris(dimethylamino)phosphonium hexafluorophosphate Bromotris(dimethylamino)phosphonium hexafluorophosphate 50296-37-2 C6H18BrF6N3P2
2-Chloro-1,3-dimethylimidazolidinium tetrafluoroborate 2-Chloro-1,3-dimethylimidazolidinium tetrafluoroborate 153433-26-2 C5H10ClN2.BF4
2-(2-Pyridon-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate 2-(2-Pyridon-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate 125700-71-2 C10H16N3O2.BF4
2-(7-Azabenzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate 2-(7-Azabenzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate 873798-09-5 C10H15BF4N6O
2-Fluoro-1,3-dimethylimidazolidinium hexafluorophosphate 2-Fluoro-1,3-dimethylimidazolidinium hexafluorophosphate 164298-27-5 C5H10FN2.F6P
Chlorodipiperidinocarbenium hexafluorophosphate Chlorodipiperidinocarbenium hexafluorophosphate 161308-40-3 C11H20ClF6N2P
(Benzotriazol-1-yloxy)dipyrrolidinocarbenium hexafluorophosphate (Benzotriazol-1-yloxy)dipyrrolidinocarbenium hexafluorophosphate 105379-24-6 C15H20F6N5OP
1,1'-Carbonyldipyrrolidine 1,1'-Carbonyldipyrrolidine 81759-25-3 C9H16N2O
Chlorotripyrrolidinophosphonium hexafluorophosphate Chlorotripyrrolidinophosphonium hexafluorophosphate 133894-48-1 C12H24ClF6N3P2
Isobutyl 1,2-dihydro-2-isobutoxy-1-quinoline-carboxylate Isobutyl 1,2-dihydro-2-isobutoxy-1-quinoline-carboxylate 38428-14-7 C18H25NO3
O-(6-Chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate O-(6-Chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 330641-16-2 C11H15BClF4N5O
7-Azabenzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate 7-Azabenzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate 156311-85-2 C11H21F6N7OP2
Ethyl 1-hydroxy-1H-1,2,3-triazole-4-carboxylate Ethyl 1-hydroxy-1H-1,2,3-triazole-4-carboxylate 137156-41-3 C5H7N3O3
N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline 16357-59-8 C14H17NO3
HNTU HNTU 208462-94-6 C14H20F6N3O3P
(Benzotriazol-1-yloxy)dipiperidinocarbenium hexafluorophosphate (Benzotriazol-1-yloxy)dipiperidinocarbenium hexafluorophosphate 190849-64-0 C17H24F6N5OP
N-(4-Aminobutyl)-N-ethylisoluminol N-(4-Aminobutyl)-N-ethylisoluminol 66612-29-1 C14H20N4O2
2-(1-Oxy-pyridin-2-yl)-1,1,3,3-tetramethylisothiouronium tetrafluoroborate 2-(1-Oxy-pyridin-2-yl)-1,1,3,3-tetramethylisothiouronium tetrafluoroborate 255825-38-8 C10H17BF4N3OS*
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