(1R,3R,4R,7S)-3-(6-Benzamido-9H-purin-9-yl)-1-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-7-yl (2-cyanoethyl) diisopropylphosphoramidite

Base Information

• Chemical Name: (1R,3R,4R,7S)-3-(6-Benzamido-9H-purin-9-yl)-1-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-7-yl (2-cyanoethyl) diisopropylphosphoramidite
• CAS No.: 206055-79-0
• Molecular Formula: C48H52N7O8P
• Molecular Weight: 885.96
• European Community (EC) Number: 686-259-6
• Nikkaji Number: J1.747.418I

Synonyms:206055-79-0;(1R,3R,4R,7S)-3-(6-Benzamido-9H-purin-9-yl)-1-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-7-yl (2-cyanoethyl) diisopropylphosphoramidite;N-[9-[(1R,3R,4R,7S)-1-[[Bis(4-methoxyphenyl)-phenylmethoxy]methyl]-7-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-2,5-dioxabicyclo[2.2.1]heptan-3-yl]purin-6-yl]benzamide;SCHEMBL1096766;EX-A7174A;MFCD22373373;DMTr-LNA-A(Bz)-3-CED-phosphoramidite;BP-40022;N6-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-LNA-adenosine-3'-cyanoethyl phosphoramidite;(1R,3R,4R,7S)-3-(6-Benzamido-9H-purin-9-yl)-1-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-7-yl(2-cyanoethyl)diisopropylphosphoramidite;N6-benzoyl-5'-O-(4, 4'-dimethoxytrityl)-2'-O-4'-C-Locked-adenosine-3'-cyanoethyl Phosphoramidite

Chemical Property of (1R,3R,4R,7S)-3-(6-Benzamido-9H-purin-9-yl)-1-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-7-yl (2-cyanoethyl) diisopropylphosphoramidite

Chemical Property:

• PKA: 7.81±0.43(Predicted)
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 19
• Exact Mass: 885.36149864
• Heavy Atom Count: 64
• Complexity: 1500

Purity/Quality:

98%,99% , ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)N(C(C)C)P(OCCC#N)OC1C2C(OC1(CO2)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC)N6C=NC7=C(N=CN=C76)NC(=O)C8=CC=CC=C8
• Isomeric SMILES: CC(C)N(C(C)C)P(OCCC#N)O[C@H]1[C@@H]2[C@@H](O[C@]1(CO2)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC)N6C=NC7=C(N=CN=C76)NC(=O)C8=CC=CC=C8
• Uses: DMT-?locA(bz) Phosphoramidite is a Locked-Nucleic Acid (LNA) oligonucleotide which is used in oligonucleotide synthesis via protected groups.

Technology Process of (1R,3R,4R,7S)-3-(6-Benzamido-9H-purin-9-yl)-1-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-7-yl (2-cyanoethyl) diisopropylphosphoramidite

There total 41 articles about (1R,3R,4R,7S)-3-(6-Benzamido-9H-purin-9-yl)-1-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-7-yl (2-cyanoethyl) diisopropylphosphoramidite 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: 63.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + (1S,3R,4S,7R)-1-[[(4,4'-dimethoxytrityl)oxy]methyl]-7-hydroxy-3-(6-N-benzoyladenin-9-yl)-2,5-dioxabicyclo[2.2.1]heptane (341536-51-4) → (1S,3R,4S,7R)-7-[2-cyanoethoxy(diisopropylamino)phosphinoxy]-1-[[(4,4'-dimethoxytrityl)oxy]methyl]-3-(6-N-benzoyladenin-9-yl)-2,5-dioxabicyclo[2.2.1]heptane (206055-79-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

DOI:10.1016/S0960-894X(01)00110-X

Reference yield:

N-benzoyladenine (4005-49-6) → (1S,3R,4S,7R)-7-[2-cyanoethoxy(diisopropylamino)phosphinoxy]-1-[[(4,4'-dimethoxytrityl)oxy]methyl]-3-(6-N-benzoyladenin-9-yl)-2,5-dioxabicyclo[2.2.1]heptane (206055-79-0)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 52 percent / SnCl₄ / acetonitrile / 4 h / 20 °C

2.1: NH₃ / methanol / 2 h / 0 °C

3.1: pyridine / toluene; CH₂Cl₂ / 2 h / -30 - 20 °C

4.1: 3.05 percent / 18-crown-6 / toluene / 0.5 h / 80 °C

5.1: NH₃ / methanol / 0.5 h / 20 °C

5.2: aq. NH₃ / methanol / 22 h / 20 °C

6.1: pyridine / 2.5 h / 20 °C

7.1: 16.5 h / 20 °C

8.1: 656 mg / aq. NH₃ / methanol / 6.5 h / 20 °C

9.1: 79 percent / pyridine / 2 h / 0 °C

10.1: NaH / tetrahydrofuran / 6.5 h / 0 °C

11.1: 911 mg / 18-crown-6 / dioxane / 19 h / Heating

12.1: 83 percent / NH₃ / methanol / 17 h / 0 °C

13.1: 44 percent / HCOONH₄; 10percent Pd/C / methanol / 12 h / Heating

14.1: 82 percent / pyridine / 11 h / 20 °C

15.1: 63 percent / pyridine; (N,N-diisopropyl)ethylamine / CH₂Cl₂ / 14.5 h / 20 °C

With pyridine; ammonium hydroxide; 18-crown-6 ether; ammonia; ammonium formate; tin(IV) chloride; sodium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; toluene; acetonitrile;

DOI:10.1021/ja0168763

Reference yield:

1,2-Di-O-acetyl-5-O-benzoyl-4-C-benzoyloxymethyl-3-O-benzyl-L-threo-pentofuranose (230631-16-0) → (1S,3R,4S,7R)-7-[2-cyanoethoxy(diisopropylamino)phosphinoxy]-1-[[(4,4'-dimethoxytrityl)oxy]methyl]-3-(6-N-benzoyladenin-9-yl)-2,5-dioxabicyclo[2.2.1]heptane (206055-79-0)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 52 percent / SnCl₄ / acetonitrile / 4 h / 20 °C

2.1: NH₃ / methanol / 2 h / 0 °C

3.1: pyridine / toluene; CH₂Cl₂ / 2 h / -30 - 20 °C

4.1: 3.05 percent / 18-crown-6 / toluene / 0.5 h / 80 °C

5.1: NH₃ / methanol / 0.5 h / 20 °C

5.2: aq. NH₃ / methanol / 22 h / 20 °C

6.1: pyridine / 2.5 h / 20 °C

7.1: 16.5 h / 20 °C

8.1: 656 mg / aq. NH₃ / methanol / 6.5 h / 20 °C

9.1: 79 percent / pyridine / 2 h / 0 °C

10.1: NaH / tetrahydrofuran / 6.5 h / 0 °C

11.1: 911 mg / 18-crown-6 / dioxane / 19 h / Heating

12.1: 83 percent / NH₃ / methanol / 17 h / 0 °C

13.1: 44 percent / HCOONH₄; 10percent Pd/C / methanol / 12 h / Heating

14.1: 82 percent / pyridine / 11 h / 20 °C

15.1: 63 percent / pyridine; (N,N-diisopropyl)ethylamine / CH₂Cl₂ / 14.5 h / 20 °C

With pyridine; ammonium hydroxide; 18-crown-6 ether; ammonia; ammonium formate; tin(IV) chloride; sodium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; toluene; acetonitrile;

DOI:10.1021/ja0168763

upstream raw materials:

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

(1S,3R,4S,7R)-1-[[(4,4'-dimethoxytrityl)oxy]methyl]-7-hydroxy-3-(6-N-benzoyladenin-9-yl)-2,5-dioxabicyclo[2.2.1]heptane

1,2-O-isopropylidene-3-O-benzyl-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose

N-benzoyladenine

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