Dmt-2'fluoro-da(bz) amidite

Base Information

• Chemical Name: Dmt-2'fluoro-da(bz) amidite
• CAS No.: 136834-22-5
• Molecular Formula: C47H51FN7O7P
• Molecular Weight: 875.92
• European Community (EC) Number: 890-259-3
• Mol file: 136834-22-5.mol

Synonyms:136834-22-5;Dmt-2'fluoro-da(bz) amidite;(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) Phosphoramidite;N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-3-fluorooxolan-2-yl]purin-6-yl]benzamide;Adenosine, N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-2'-fluoro-, 3'-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite];DMT-2'Fluoro-dA(bz) Phosphoramidite, configured for ABI;MFCD12912392;C47H51FN7O7P;SCHEMBL18927153;CS-B1581;AKOS027251134;DMT-2'-Fluoro-dA(Bz) Phosphoramidite;AS-75211;HY-21997;PD157913;C72479;A858248;J-700058;2'-Fluoro-N6-Bz-5'-O-DMT-2'-dA-3'-CE-phosphoramidite;DMT-2'Fluoro-dA(bz) Phosphoramidite, configured for MerMade;DMT-2'Fluoro-dA(bz) Phosphoramidite, configured for (??KTA(R) and OligoPilot(R));(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;N-Benzoyl-5'-O-(4,4'-Dimethoxytrityl)-3'-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-2'-deoxy-2'-fluoroadenosine;N6-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-fluoro-2'-deoxyadenosine-3'-(2-cyanoethyl diisopropylphosphoramidite)

Chemical Property of Dmt-2'fluoro-da(bz) amidite

Chemical Property:

• PKA: 7.87±0.43(Predicted)
• PSA: 168.70000
• LogP: 9.07418
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 7.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 19
• Exact Mass: 875.35716215
• Heavy Atom Count: 63
• Complexity: 1420

Purity/Quality:

98% ^*data from raw suppliers

(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 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)N(C(C)C)P(OCCC#N)OC1C(OC(C1F)N2C=NC3=C(N=CN=C32)NC(=O)C4=CC=CC=C4)COC(C5=CC=CC=C5)(C6=CC=C(C=C6)OC)C7=CC=C(C=C7)OC
• Isomeric SMILES: CC(C)N(C(C)C)P(OCCC#N)O[C@@H]1[C@H](O[C@H]([C@@H]1F)N2C=NC3=C(N=CN=C32)NC(=O)C4=CC=CC=C4)COC(C5=CC=CC=C5)(C6=CC=C(C=C6)OC)C7=CC=C(C=C7)OC
• 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 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.

Technology Process of Dmt-2'fluoro-da(bz) amidite

There total 20 articles about Dmt-2'fluoro-da(bz) amidite 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: 78.0%

2-(Cyanethoxy)-bis-N,N-(diisopropylamino)phosphane + N-(9-((2R,3R,4R,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)3-fluoro-4-hydroxytetrahydrofuran-2-yl)9H-purin-6yl)benzamide triethylammonium salt (136834-21-4) → N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenyl-methoxy]methyl]-4-[2-cyanoethoxy-(diisopropylamino)phosphanyl]oxy-3-fluoro-tetrahydrofuran-2-yl]purin-6-yl]benzamide (136834-22-5,329187-86-2)

Guidance literature:

With N,N-diisopropylamine tetrazolide; In dichloromethane; at 23 ℃; for 8h;

DOI:10.1021/jm00059a007

Reference yield: 72.0%

9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine (20187-82-0,20227-41-2,64183-27-3,123334-75-8) + 4,4'-dimethoxytrityl chloride (40615-36-9) + benzoyl chloride (98-88-4) → (2R,3R,4S,5R)-5-(6-benzamido-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-fluorotetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite (136834-22-5,329187-86-2)

Guidance literature:

9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine; benzoyl chloride; With pyridine; at 20 ℃; for 18h;

4,4'-dimethoxytrityl chloride; In pyridine; at 20 ℃; for 18h;

PN(iPr)2(OCH₂CH₂CN)X;

DOI:10.1080/15257770008045466

Reference yield:

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1) + N-(9-((2R,3R,4R,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)3-fluoro-4-hydroxytetrahydrofuran-2-yl)9H-purin-6yl)benzamide triethylammonium salt (136834-21-4) → N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenyl-methoxy]methyl]-4-[2-cyanoethoxy-(diisopropylamino)phosphanyl]oxy-3-fluoro-tetrahydrofuran-2-yl]purin-6-yl]benzamide (136834-22-5,329187-86-2)

Guidance literature:

With DCI; In dichloromethane; at 0 - 25 ℃; for 3h;

upstream raw materials:

N-(9-((2R,3R,4R,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)3-fluoro-4-hydroxytetrahydrofuran-2-yl)9H-purin-6yl)benzamide triethylammonium salt

N6-benzoyl-9-β-D-arabinofuranosyladenine

N-(9-((2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide

N⁶-benzoyl-9-(3,5-di-O-tetrahydropyran-2-yl-β-D-arabinofuranosyl)adenine

Refernces

• 1、 -. "CYCLIC DI-NUCLEOTIDES AS STIMULATOR OF INTERFERON GENES MODULATORS". Paragraph 00832; 00835; 00836. . Retrieved 2019/03/17.
• 2、 -. "Antisense modulation of polo-like kinase expression". Page/Page column 18. . Retrieved 2008/06/13.