DMT-2'-F-dGiBu

Base Information

• Chemical Name: DMT-2'-F-dGiBu
• CAS No.: 144089-96-3
• Molecular Formula: C35H36FN5O7
• Molecular Weight: 657.699
• Mol file: 144089-96-3.mol

Synonyms:N2-isobutyryl-5'-0-(4,4'-dimethoxytrityl)-2'-fluoro-2'-deoxyguanosine;N-(9-{(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-fluoro-4-hydroxy-tetrahydro-furan-2-yl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-isobutyramide;N2-isobutyryl-2'-deoxy-2'-fluoro-5'-O-(4,4'-dimethoxytrityl)guanosine;

Chemical Property of DMT-2'-F-dGiBu

Chemical Property:

• PKA: 9.16±0.20(Predicted)
• PSA: 149.82000
• Density: 1.38±0.1 g/cm3(Predicted)
• LogP: 4.40940
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

5''-O-Dmt-N2-Isobutyryl-2''-Fluoro-2''-Deoxyguanosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of DMT-2'-F-dGiBu

There total 12 articles about DMT-2'-F-dGiBu which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + 2’-fluoro-N2-isobutyryl-2’-deoxyguanosine (80681-25-0) → N-(9-((2R,3R,4R,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-fluoro-4-hydroxytetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide (144089-96-3)

Guidance literature:

With pyridine; triethylamine; at 23 ℃; for 4h;

DOI:10.1021/jm00059a007

Reference yield:

(2R,3R,4R,5R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-fluoro-5-(2-isobutyramido-6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite → (2R,3R,4R,5R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-fluoro-5-(2-isobutyramido-6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuran-3-yl hydrogen phosphonate + N-(9-((2R,3R,4R,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-fluoro-4-hydroxytetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide (144089-96-3)

Guidance literature:

(2R,3R,4R,5R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-fluoro-5-(2-isobutyramido-6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite; With water; pyridinium trifluroacetate; In acetonitrile; for 0.0166667h;

With tert-butylamine; In acetonitrile; for 0.166667h;

With pyridine; 2-Chloro-4H-1,3,2-benzodioxaphosphorin-4-one; In 1,4-dioxane; for 0.25h;

Reference yield:

3',5'-O-1,1,3,3-tetraisopropyldisiloxan-1,3-diyl-guanosine (69304-44-5) → N-(9-((2R,3R,4R,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-fluoro-4-hydroxytetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide (144089-96-3)

Guidance literature:

Multi-step reaction with 10 steps

1: DMSO, acetic anhydride

2: NaBH₄ / 1.5 h / 0 °C

3: 80 percent / pyridine / 20 h / 60 °C

4: 80 percent / n-Bu₄NF

5: 82 percent / p-toluenesulfonic acid / dioxane / 2 h / 23 °C

6: 78 percent / NaOH / acetonitrile; methanol; H₂O

7: pyridine, (N,N-dimethylamino)pyrydine / CH₂Cl₂ / 1 h / 5 °C

8: tertbutylammonium fluoride / tetrahydrofuran / 5 h / 5 °C

9: 41 percent / Dowex 50W x 2-100 / methanol / 1 h / 23 °C

10: 87 percent / pyridine, Et₃N / 4 h / 23 °C

With pyridine; sodium hydroxide; sodium tetrahydroborate; tert-butyl-ammonium fluoride; (N,N-dimethylamino)pyrydine; Dowex 50W x 2-100; tetrabutyl ammonium fluoride; acetic anhydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetonitrile;

DOI:10.1021/jm00059a007

upstream raw materials:

4,4'-dimethoxytrityl chloride

2’-fluoro-N2-isobutyryl-2’-deoxyguanosine

3',5'-O-1,1,3,3-tetraisopropyldisiloxan-1,3-diyl-guanosine

2-amino-9-((6aR,8R,9aR)-2,2,4,4-tetraisopropyl-9-oxotetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-1H-purin-6(9H)-one

Downstream raw materials:

C₄₄H₄₃FN₈O₉

Refernces

• 1、 -. "COMPOSITIONS AND METHODS FOR ACTIVATING "STIMULATOR OF INTERFERON GENE"-DEPENDENT SIGNALLING". Paragraph 00492; 00493. . Retrieved 2017/05/17.
• 2、 Kawasaki,Casper,Freier,Lesnik,Zounes,Cummins,Gonzalez,Cook. "Uniformly modified 2'-deoxy-2'-fluoro phosphorothioate oligonucleotides as nuclease-resistant antisense compounds with high affinity and specificity for RNA targets". . p. 831 - 841. Retrieved 2007/10/02.