3-methyl-2-[(N-phenoxyacetyl)amino]-5-{5'-O-[(4,4'-dimethoxytriphenyl)methyl]-2'-deoxy-β-D-ribofuranosyl}pyridine

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Chemical Name:3-methyl-2-[(N-phenoxyacetyl)amino]-5-{5'-O-[(4,4'-dimethoxytriphenyl)methyl]-2'-deoxy-β-D-ribofuranosyl}pyridine
CAS No.:190907-98-3
Molecular Formula:C₄₀H₄₀N₂O₇
Molecular Weight:660.767
Hs Code.:

Synonyms:3-methyl-2-[(N-phenoxyacetyl)amino]-5-{5'-O-[(4,4'-dimethoxytriphenyl)methyl]-2'-deoxy-β-D-ribofuranosyl}pyridine

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Chemical Property of 3-methyl-2-[(N-phenoxyacetyl)amino]-5-{5'-O-[(4,4'-dimethoxytriphenyl)methyl]-2'-deoxy-β-D-ribofuranosyl}pyridine

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Technology Process of 3-methyl-2-[(N-phenoxyacetyl)amino]-5-{5'-O-[(4,4'-dimethoxytriphenyl)methyl]-2'-deoxy-β-D-ribofuranosyl}pyridine

There total 10 articles about 3-methyl-2-[(N-phenoxyacetyl)amino]-5-{5'-O-[(4,4'-dimethoxytriphenyl)methyl]-2'-deoxy-β-D-ribofuranosyl}pyridine 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: 74.0%

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 190907-93-8
3-methyl-2-[N-(phenoxyacetyl)amino]-5-(2'-deoxy-β-D-ribofuranosyl)pyridine

: 190907-98-3
3-methyl-2-[(N-phenoxyacetyl)amino]-5-{5'-O-[(4,4'-dimethoxytriphenyl)methyl]-2'-deoxy-β-D-ribofuranosyl}pyridine

Guidance literature:: In pyridine; for 2h;
DOI:10.1021/ja9704904

Reference yield:

: 14316-61-1
phenoxyacetic anhydride

: 190907-98-3
3-methyl-2-[(N-phenoxyacetyl)amino]-5-{5'-O-[(4,4'-dimethoxytriphenyl)methyl]-2'-deoxy-β-D-ribofuranosyl}pyridine

Guidance literature:: Multi-step reaction with 7 steps

1: 67 percent / pyridine / 4.5 h / Ambient temperature

2: 81 percent / BBr₃ / CH₂Cl₂ / 5 h / -75 °C

3: 84 percent / pyridine / 4 h / Ambient temperature

4: 74 percent / dimethylformamide / rt, 1h, 40 deg C, 3.5 h

5: 67 percent / AIBN, SiH(SiMe₃)2 / toluene / 5 h / 80 °C

6: 93 percent / Bu₄NF / tetrahydrofuran / 1.5 h / Ambient temperature

7: 74 percent / pyridine / 2 h

With 2,2'-azobis(isobutyronitrile); 1,1,1,3,3,3-hexamethyltrisilane; tetrabutyl ammonium fluoride; boron tribromide; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja9704904

Reference yield:

: 3430-21-5
5-bromo-3-methyl-pyridin-2-ylamine

: 190907-98-3
3-methyl-2-[(N-phenoxyacetyl)amino]-5-{5'-O-[(4,4'-dimethoxytriphenyl)methyl]-2'-deoxy-β-D-ribofuranosyl}pyridine

Guidance literature:: Multi-step reaction with 9 steps

1: 69 percent / ZnI₂ / 15 h / 140 °C

2: 1.) n-BuLi, 2.) Et₃SiH, BF₃*Et₂O / 1.) THF, -75 deg C, 3 h, -75 deg C -> 0 deg C, 4 h, 2.) CH₂Cl₂, -75 deg C -> rt, overnight

3: 67 percent / pyridine / 4.5 h / Ambient temperature

4: 81 percent / BBr₃ / CH₂Cl₂ / 5 h / -75 °C

5: 84 percent / pyridine / 4 h / Ambient temperature

6: 74 percent / dimethylformamide / rt, 1h, 40 deg C, 3.5 h

7: 67 percent / AIBN, SiH(SiMe₃)2 / toluene / 5 h / 80 °C

8: 93 percent / Bu₄NF / tetrahydrofuran / 1.5 h / Ambient temperature

9: 74 percent / pyridine / 2 h

With triethylsilane; n-butyllithium; 2,2'-azobis(isobutyronitrile); 1,1,1,3,3,3-hexamethyltrisilane; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; boron tribromide; zinc(II) iodide; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja9704904