DMT-dA(bz) Phosphoramidite Chemical Properties

Density 

1.23 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

7.87±0.43(Predicted)

color 

white to off-white

biological source

non-animal source (no BSE/TSE risk)

Water Solubility 

soluble, clear

InChI

InChI=1S/C47H52N7O7P/c1-32(2)54(33(3)4)62(59-27-13-26-48)61-40-28-42(53-31-51-43-44(49-30-50-45(43)53)52-46(55)34-14-9-7-10-15-34)60-41(40)29-58-47(35-16-11-8-12-17-35,36-18-22-38(56-5)23-19-36)37-20-24-39(57-6)25-21-37/h7-12,14-25,30-33,40-42H,13,27-29H2,1-6H3,(H,49,50,52,55)/t40-,41+,42+,62?/m0/s1

InChIKey

GGDNKEQZFSTIMJ-AKWFTNRHSA-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](N2C3C(=C(N=CN=3)NC(=O)C3=CC=CC=C3)N=C2)C[C@@H]1OP(N(C(C)C)C(C)C)OCCC#N

LogP

7.14 at 20℃

Safety Information

WGK Germany 

3

HS Code 

29349990

DMT-dA(bz) Phosphoramidite Usage And Synthesis

Physical form

Powder or granules

Color

White to off-white

General Description

DMT-dA(bz) Phosphoramidite belongs to the group of DNA Phosphoramidites. Its key features include:
Exocyclic amine functions are protected by a benzoyl group (dA(bz) anddC(bz)) or isobutyryl group (dG(ib)).
Recommended cleavage and deprotection conditions are 8 hours at 55 °Cor 24 hours at room temperature using concentrated ammonia solution,for standard base-protected oligonucleotides.
The high coupling efficiency of Proligo′s DNA phosphoramidites leads tohigh-yield and high-quality oligonucleotides.

Uses

N6-Benzoyl-2’-deoxy-5’-O-DMT-cytidine 3’-CE Phosphoramidite is used to prepare antisense oligonucleotides containing conformationally constrained methoxyaminomethylene and aminooxymethylene and aminomethylene bridged nucleoside analogs.

Synthesis

Synthesis of (2R,3S,5R)-5-(6-benzoylamino-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide from N-(9-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4- hydroxytetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide: The general procedure for synthesizing (2R,3S,5R)-5-(6-benzoylamino-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl) Methoxy)methyl)tetrahydrofuran-3-yl(2-cyanoethyl)diisopropylphosphoramidite was carried out in the following general steps: the nucleoside was phosphorylated using the N-methylimidazole salts of [O-β-cyanoethyl-N,N,N',N'-tetraisopropylphosphoramidite] and saccharin as the activators. This was done as follows: nucleoside (1.5 mmol) was added in a flask of appropriate size and the solid was dried by azeotropic distillation twice (using a rotary evaporator) with 20 mL of pyridine. After purging the flask with argon, 15 mL of acetonitrile was added. The mixture was stirred at room temperature until a clarified solution was formed. Subsequently, [O-β-cyanoethyl-N,N,N',N'-tetraisopropylphosphoramidite] (Tetraphos) was added to the solution, followed by the N-methylimidazole salt of saccharin. The reaction mixture was stirred continuously at room temperature and the progress of the reaction was monitored by HPLC. Upon completion of the reaction, the mixture was diluted with 30 mL of ethyl acetate and the organic phase was washed sequentially with 2 x 25 mL of saturated aqueous sodium bicarbonate and 25 mL of saturated aqueous sodium chloride. The organic layer was separated and dried with anhydrous magnesium sulfate. The dried suspension was filtered and the solvent was removed using a rotary evaporator. Finally, the residue was dried under vacuum to obtain the target product as a foamy solid.

References

[1] Patent: WO2004/35599, 2004, A1. Location in patent: Page 9-10
[2] Patent: WO2004/35599, 2004, A1. Location in patent: Page 10-11

DMT-dA(bz) Phosphoramidite(98796-53-3)Related Product Information

• 3-Mercaptopropyltriethoxysilane
• 3-Chloropropyltrimethoxysilane
• Benzoyl peroxide
• Vidarabine
• Trimethoxypropylsilane
• Adenosine5'-(tetrahydrogen triphosphate), disodiuM salt, trihydrate (9CI)
• 3-Aminopropyltriethoxysilane
• ADENOSINE 5'-TRIPHOSPHATASE
• 3-Chloropropyltriethoxysilane
• 2'-Deoxyadenosine monohydrate
• Cyclic AMP
• Benzoyl chloride
• Adenosine
• 2'-Deoxyadenosine
• 5'-Deoxyadenosylcobalamin
• DMT-2'O-TBDMS-rA(bz) Phosphoramidite
• N6-Benzoyl-2'-deoxyadenosine
• 5'-O-FDMT-N6-BENZOYL-2'-DEOXYADENOSINE CEP