DMT-dT Phosphoramidite Chemical Properties

Density 

1.22 at 20℃

vapor pressure 

0-0Pa at 20-50℃

storage temp. 

Sealed in dry,2-8°C

solubility 

soluble, clear

form 

powder or granules

pka

9.55±0.10(Predicted)

color 

white to off-white

biological source

non-animal source (no BSE/TSE risk)

Water Solubility 

soluble, clear

InChI

InChI=1/C40H49N4O8P/c1-27(2)44(28(3)4)53(50-23-11-22-41)52-35-24-37(43-25-29(5)38(45)42-39(43)46)51-36(35)26-49-40(30-12-9-8-10-13-30,31-14-18-33(47-6)19-15-31)32-16-20-34(48-7)21-17-32/h8-10,12-21,25,27-28,35-37H,11,23-24,26H2,1-7H3,(H,42,45,46)/t35-,36+,37+,53?/s3

InChIKey

UNOTXUFIWPRZJX-DJKSPSSYNA-N

SMILES

O(C(C1=CC=C(OC)C=C1)(C1=CC=C(OC)C=C1)C1=CC=CC=C1)C[C@H]1O[C@@H](N2C=C(C)C(=O)NC2=O)C[C@@H]1OP(N(C(C)C)C(C)C)OCCC#N |&1:25,27,38,r|

LogP

5.8 at 20℃

Safety Information

WGK Germany 

3

HS Code 

29349990

DMT-dT Phosphoramidite Usage And Synthesis

Uses

5''-O-[Bis(4-Methoxyphenyl)phenylmethyl]-thymidine 3''-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite] is a nucleotide and reactant used in the solid-phase synthesis of phosphorothioate oligonucleotides, and in the synthesis of lipophilic 5''-phosphoramidate derivatives of DNA and RNA oligonucleotides.

Chemical Properties

5'-O-DMT-Thymidine-CE Phosphoramidite is also known as DMT-dT Phosphoramidite. The IUPAC Name of this compound is (2R,3S,5R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite. It allows for the introduction of thymidine units into oligonucleotides. Also, it has been used in various applications, including the synthesis of natural and unnatural DNA and RNA strands.

Synthesis

General synthesis of (2R,3S,5R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuro-3-yl(2-cyanoethyl)diisopropyl phosphoramidite, starting with bis(diisopropylamino)(2-cyanoethoxy)phosphine and protecting thymidine The steps are as follows: with reference to Comparative Examples 1-3; three different phosphoramidite reactions (C1-C3) were carried out to react the protecting nucleoside reagent with 2-cyanoethyl-N,N,N',N'-tetraisopropylphosphoramidite in the presence of a pyridine-TFA activator and the yields were calculated for each of the reactions. The general procedure of Examples 12-18 was followed. Table 3 lists the different combinations of protected nucleosides, solvents and yields for the three reactions. As shown in Table 3, the yields of the present invention are surprisingly at least comparable, and in many cases superior, to similar reactions using conventional activators containing significantly less hindered unsubstituted pyridine salts.

References

[1] Chemical Communications, 1997, # 9, p. 877 - 878
[2] Tetrahedron Letters, 1990, vol. 31, # 10, p. 1463 - 1466
[3] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 4, p. 747 - 757
[4] Patent: US2003/232980, 2003, A1. Location in patent: Page 7
[5] Patent: US2003/232980, 2003, A1. Location in patent: Page 6

DMT-dT Phosphoramidite(98796-51-1)Related Product Information

• Phenyltriethoxysilane
• Diphenyldimethoxysilane
• 2,3-Dimethylbutane
• Thymidine
• Diisopropyl ether
• N,N-Diisopropylethylamine
• 4-Methoxyphenylacetone
• Trimethoxypropylsilane
• 3-Aminopropyltriethoxysilane
• p-(2-Methoxyethyl) phenol
• FLUORESCEIN-DT CEP
• 5-ETHYNYL-DU CEP
• NPOM-CAGED-DT CEP
• BBQ-650-DT CEP
• DABCYL-DT CEP
• 2'-O-METHYL-5-METHYL-U CEP
• 5'-O-FDMT-THYMIDINE CEP
• 5-METHOXYMETHYL-DU CEP