(2R,3R,4R,5R)-2-((BIS(4-METHOXYPHENYL)(PHENYL)METHOXY)METHYL)-4-(2-METHOXYETHOXY)-5-(5-METHYL-2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)TETRAHYDROFURAN-3-YL 2-CYANOETHYL DIISOPROPYLPHOSPHORAMIDITE

Base Information

• Chemical Name: (2R,3R,4R,5R)-2-((BIS(4-METHOXYPHENYL)(PHENYL)METHOXY)METHYL)-4-(2-METHOXYETHOXY)-5-(5-METHYL-2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)TETRAHYDROFURAN-3-YL 2-CYANOETHYL DIISOPROPYLPHOSPHORAMIDITE
• CAS No.: 163878-63-5
• Molecular Formula: C₄₃H₅₅N₄O₁₀P
• Molecular Weight: 818.904
• Mol file: 163878-63-5.mol

Synonyms:5'-O-[BIS(4-METHOXYPHENYL)PHENYLMETHYL]-2'-O-METHYL-5-METHYLURIDINE;5'-O-DMT-2'-O-METHYL-5-METHYLURIDINE;5'-O-(Dimethoxytrityl)-2'-o-methyl-5-methyluridine;

Chemical Property of (2R,3R,4R,5R)-2-((BIS(4-METHOXYPHENYL)(PHENYL)METHOXY)METHYL)-4-(2-METHOXYETHOXY)-5-(5-METHYL-2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)TETRAHYDROFURAN-3-YL 2-CYANOETHYL DIISOPROPYLPHOSPHORAMIDITE

Chemical Property:

• PKA: 9.55±0.10(Predicted)
• PSA: 169.32000
• LogP: 6.46108

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2R,3R,4R,5R)-2-((BIS(4-METHOXYPHENYL)(PHENYL)METHOXY)METHYL)-4-(2-METHOXYETHOXY)-5-(5-METHYL-2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)TETRAHYDROFURAN-3-YL 2-CYANOETHYL DIISOPROPYLPHOSPHORAMIDITE

There total 16 articles about (2R,3R,4R,5R)-2-((BIS(4-METHOXYPHENYL)(PHENYL)METHOXY)METHYL)-4-(2-METHOXYETHOXY)-5-(5-METHYL-2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)TETRAHYDROFURAN-3-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: 95.0%

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1) + 5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(2-methoxyethyl)-5-methyluridine (163759-50-0) → [5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(2-methoxyethyl)-5-methyluridin-3'-O-yl]-2-cyanoethyl-N,N-diisopropylphosphoramidite (163759-51-1,163759-59-9,163878-63-5)

Guidance literature:

With 1-methyl-1H-imidazole; 1H-tetrazole; In DMF (N,N-dimethyl-formamide); toluene; at 20 ℃; for 5h;

Reference yield:

O-2,2'-cyclo-5-methyluridine (22423-26-3) → [5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(2-methoxyethyl)-5-methyluridin-3'-O-yl]-2-cyanoethyl-N,N-diisopropylphosphoramidite (163759-51-1,163759-59-9,163878-63-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydrogencarbonate / 2-methoxy-ethanol / 21 h / 130 °C

1.2: 0.5 h / Heating / reflux

2.1: lutidine / acetonitrile / 1.42 h / -10 - 3 °C

3.1: 1-methyl-1H-imidazole; 1H-tetrazole / 5 h / 20 °C

With 1-methyl-1H-imidazole; 1H-tetrazole; lutidine; sodium hydrogencarbonate; In 2-methoxy-ethanol; acetonitrile;

Reference yield:

D-ribose (50-69-1) → [5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(2-methoxyethyl)-5-methyluridin-3'-O-yl]-2-cyanoethyl-N,N-diisopropylphosphoramidite (163759-51-1,163759-59-9,163878-63-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) cc. H₂SO₄, 2.) NaH / 1.) 4 deg C, 16 h, 2.) DMF, 40 deg C

2: 125.9 g / SnCl₄ / CH₂Cl₂ / 35 h / 3 °C

3: pyridine, 4-(dimethylamino)-pyridine / 17 h

4: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) TfOSiMe₃ / 1.) ClCH₂CH₂Cl, reflux, 10 min, 2.) ClCH₂CH₂Cl, 70 deg C, 20 h

5: 1,8-diazabicyclo<5.4.0>undec-7-ene / acetonitrile / 10 h

6: 98 percent / 30percent NaOMe / methanol / 3 h / Ambient temperature

7: 83 percent / NaH / tetrahydrofuran / 40 - 70 °C

8: H₂ / 5percent Pd/C / tetrahydrofuran / Ambient temperature

9: 30percent NaOMe / methanol / Ambient temperature; pH 11

10: 94 percent / H₂, NaOAc / 5percent Pd/C / methanol / 45 °C / 2250.2 Torr

11: pyridine / 5 h / Ambient temperature

12: 89 percent / diisopropylammonium-tetrazolide / CH₂Cl₂ / Ambient temperature

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; N,N-diisopropylamine tetrazolide; hydrogen; sodium methylate; sodium acetate; tin(IV) chloride; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1002/hlca.19950780219

upstream raw materials:

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite

5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(2-methoxyethyl)-5-methyluridine

D-ribose

4,4'-dimethoxytrityl chloride