3',5'-di-O-benzyl-3-N-(benzyloxymethyl)-3'-C-((methoxymethoxy)methyl)-4'-C-(p-toluenesulfonyloxymethyl)thymidine

Base Information

• Chemical Name: 3',5'-di-O-benzyl-3-N-(benzyloxymethyl)-3'-C-((methoxymethoxy)methyl)-4'-C-(p-toluenesulfonyloxymethyl)thymidine
• CAS No.: 950755-33-6
• Molecular Formula: C₄₃H₄₈N₂O₁₁S
• Molecular Weight: 800.927
• Mol file: 950755-33-6.mol

Synonyms:3',5'-di-O-benzyl-3-N-(benzyloxymethyl)-3'-C-((methoxymethoxy)methyl)-4'-C-(p-toluenesulfonyloxymethyl)thymidine

Chemical Property of 3',5'-di-O-benzyl-3-N-(benzyloxymethyl)-3'-C-((methoxymethoxy)methyl)-4'-C-(p-toluenesulfonyloxymethyl)thymidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3',5'-di-O-benzyl-3-N-(benzyloxymethyl)-3'-C-((methoxymethoxy)methyl)-4'-C-(p-toluenesulfonyloxymethyl)thymidine

There total 14 articles about 3',5'-di-O-benzyl-3-N-(benzyloxymethyl)-3'-C-((methoxymethoxy)methyl)-4'-C-(p-toluenesulfonyloxymethyl)thymidine 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: 100.0%

p-toluenesulfonyl chloride (98-59-9) + 3',5'-di-O-benzyl-3-N-(benzyloxymethyl)-4'-C-(hydroxymethyl)-3'-C-((methoxymethoxy)methyl)thymidine (583843-95-2) → 3',5'-di-O-benzyl-3-N-(benzyloxymethyl)-3'-C-((methoxymethoxy)methyl)-4'-C-(p-toluenesulfonyloxymethyl)thymidine (950755-33-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 13h;

DOI:10.1016/j.tet.2007.06.040

Reference yield:

3'-deoxy-3'-C-methylidene-5'-O-(triphenylmethyl)thymidine (131607-35-7) → 3',5'-di-O-benzyl-3-N-(benzyloxymethyl)-3'-C-((methoxymethoxy)methyl)-4'-C-(p-toluenesulfonyloxymethyl)thymidine (950755-33-6)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 65 percent / N-methylmorpholine N-oxide; pyridine; H₂O / osmium tetroxide / 2-methyl-propan-2-ol / 8 h / 75 °C

2.1: 89 percent / DBU / dimethylformamide / 5 h / 20 °C

3.1: dibutyltin dimethoxide / dioxane / 5 h / Heating

3.2: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 2 h / 20 °C

4.1: 84 percent / NaH; n-Bu₄NI / dimethylformamide / 6 h / 20 °C

5.1: 90 percent / (+)-10-camphorsulfonic acid; MeOH / CH₂Cl₂ / 9 h / 20 °C

6.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

7.1: NaOH / tetrahydrofuran; H₂O / 2.5 h / 15 °C

8.1: sodium borohydride / tetrahydrofuran; H₂O / 2 h / 0 °C

9.1: 99 percent / (+)-10-camphorsulfonic acid / CH₂Cl₂ / 2 h / 20 °C

10.1: 30 percent / triethylsilane; boron trifluoride diethyl etherate / CH₂Cl₂ / 0 °C

11.1: 100 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 13 h / 20 °C

With pyridine; methanol; triethylsilane; dmap; sodium hydroxide; sodium tetrahydroborate; boron trifluoride diethyl etherate; water; tetra-(n-butyl)ammonium iodide; sodium hydride; dibutyldimethoxytin; Dess-Martin periodane; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; (+)-10-camphorsulfonic acid; triethylamine; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 6.1: Dess-Martin oxidation;

DOI:10.1016/j.tet.2007.06.040

Reference yield:

C29H34N2O9 → 3',5'-di-O-benzyl-3-N-(benzyloxymethyl)-3'-C-((methoxymethoxy)methyl)-4'-C-(p-toluenesulfonyloxymethyl)thymidine (950755-33-6)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium borohydride / tetrahydrofuran; H₂O / 2 h / 0 °C

2: 99 percent / (+)-10-camphorsulfonic acid / CH₂Cl₂ / 2 h / 20 °C

3: 30 percent / triethylsilane; boron trifluoride diethyl etherate / CH₂Cl₂ / 0 °C

4: 100 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 13 h / 20 °C

With triethylsilane; dmap; sodium tetrahydroborate; boron trifluoride diethyl etherate; (+)-10-camphorsulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/j.tet.2007.06.040

upstream raw materials:

p-toluenesulfonyl chloride

3',5'-di-O-benzyl-3-N-(benzyloxymethyl)-4'-C-(hydroxymethyl)-3'-C-((methoxymethoxy)methyl)thymidine

C₅₀H₅₄N₂O₁₁

C₅₇H₆₀N₂O₁₁

Downstream raw materials:

3',5'-di-O-benzyl-3-N-(benzyloxymethyl)-3'-C-(hydroxymethyl)-4'-C-(p-toluenesulfonyloxymethyl)thymidine

C₄₁H₄₂N₂O₁₀S

3',5'-di-O-benzyl-3-N-(benzyloxymethyl)-3'-C-(2-methoxyethenyl)-4'-C-(p-toluenesulfonyloxymethyl)thymidine

C₄₂H₄₄N₂O₁₀S