Dmt-2'fluoro-da(bz) amidite Chemical Properties

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

form 

Powder

pka

7.87±0.43(Predicted)

InChI

InChI=1/C47H51FN7O7P/c1-8-60-63(55(31(2)3)46(4,5)28-49)62-41-38(61-45(39(41)48)54-30-52-40-42(50-29-51-43(40)54)53-44(56)32-15-11-9-12-16-32)27-59-47(33-17-13-10-14-18-33,34-19-23-36(57-6)24-20-34)35-21-25-37(58-7)26-22-35/h9-26,29-31,38-39,41,45H,8,27H2,1-7H3,(H,50,51,53,56)/t38-,39-,41-,45-,63?/s3

InChIKey

ZDIBABNMVQPXHU-JWQXGDSTNA-N

SMILES

C(NC1C2=C(N=CN=1)N([C@H]1[C@H](F)[C@H](OP(OCC)N(C(C)C)C(C#N)(C)C)[C@@H](COC(C3=CC=C(OC)C=C3)(C3=CC=C(OC)C=C3)C3=CC=CC=C3)O1)C=N2)(=O)C1=CC=CC=C1 |&1:9,10,12,27,r|

Dmt-2'fluoro-da(bz) amidite Usage And Synthesis

Chemical Properties

White to Light yellow powder to crystal.

Uses

(2R,3R,4R,5R)-5-(6-Benzamido-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-fluorotetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite (Dmt-2'fluoro-da(bz) amidite) is an adenosine derivative used in the preparation of modified nucleotides to improve metabolic stability and ellicit gene silencing, and in the synthesis of microRNA inhibitors.

Synthesis

3-((Bis(diisopropylamine)phosphanyl)oxy)propanenitrile (6.42 g, 21.3 mmol, 6.77 mL, 1.8 eq) was added to a solution of N-(9-((2R,3R,4R,5R)-5-((bis(4- methoxyphenyl)(phenyl)methoxy)methyl)-3-fluoro-4-hydroxytetrahydrofuran-2-yl)-9H- purine-6-yl)benzamide (8.0 g, 11.8 mmol, 1.0 eq) in DCM (42 mL) at 0 °C followed by DCI (2.24 g, 18.9 mmol, 1.6 eq). The mixture was warmed to 25 °C and stirred for 3 hours. Two parallel reactions were carried out. The combined remedies were then diluted with DCM (150 mL), the organic layer was washed with sat NaHCO3 solution (200 mL) and brine (100 mL), dried over Na2SO4, filtered and concentrated, the crude was purified by column chromatography to give Dmt-2'fluoro-da(bz) amidite (18.0 g, 18.5 mmol, 78.1% yield, 90% purity) as a white solid.