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

Base Information

Chemical Name:3',5'-di-O-benzyl-3-N-(benzyloxymethyl)-3'-C-(2-hydroxyethyl)-4'-C-(p-toluenesulfonyloxymethyl)thymidine
CAS No.:950755-36-9
Molecular Formula:C₄₂H₄₆N₂O₁₀S
Molecular Weight:770.901
Hs Code.:

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

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Chemical Property of 3',5'-di-O-benzyl-3-N-(benzyloxymethyl)-3'-C-(2-hydroxyethyl)-4'-C-(p-toluenesulfonyloxymethyl)thymidine

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Technology Process of 3',5'-di-O-benzyl-3-N-(benzyloxymethyl)-3'-C-(2-hydroxyethyl)-4'-C-(p-toluenesulfonyloxymethyl)thymidine

There total 19 articles about 3',5'-di-O-benzyl-3-N-(benzyloxymethyl)-3'-C-(2-hydroxyethyl)-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:

: 131607-35-7
3'-deoxy-3'-C-methylidene-5'-O-(triphenylmethyl)thymidine

: 950755-36-9
3',5'-di-O-benzyl-3-N-(benzyloxymethyl)-3'-C-(2-hydroxyethyl)-4'-C-(p-toluenesulfonyloxymethyl)thymidine

Guidance literature:: Multi-step reaction with 16 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

12.1: 97 percent / TMSBr / CH₂Cl₂ / 24 h / -30 - 0 °C

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

14.1: LiHMDS / tetrahydrofuran; hexane / 0.33 h / 20 °C

14.2: 103 mg / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

15.1: H₂O; mercury(II) acetate; n-Bu₄NI / tetrahydrofuran / 19 h / 20 °C

16.1: 325 mg / sodium borohydride / tetrahydrofuran; H₂O / 0.25 h / 0 °C

With pyridine; methanol; triethylsilane; dmap; sodium hydroxide; sodium tetrahydroborate; trimethylsilyl bromide; boron trifluoride diethyl etherate; mercury(II) diacetate; 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; lithium hexamethyldisilazane; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 6.1: Dess-Martin oxidation / 13.1: Dess-Martin oxidation / 14.2: Wittig reaction;
DOI:10.1016/j.tet.2007.06.040

Reference yield:

: 1054594-66-9
C₄₂H₄₄N₂O₁₀S

: 950755-36-9
3',5'-di-O-benzyl-3-N-(benzyloxymethyl)-3'-C-(2-hydroxyethyl)-4'-C-(p-toluenesulfonyloxymethyl)thymidine

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; water; at 0 ℃; for 0.25h;
DOI:10.1016/j.tet.2007.06.040

Reference yield:

: C₂₉H₃₄N₂O₉

: 950755-36-9
3',5'-di-O-benzyl-3-N-(benzyloxymethyl)-3'-C-(2-hydroxyethyl)-4'-C-(p-toluenesulfonyloxymethyl)thymidine

Guidance literature:: Multi-step reaction with 9 steps

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

2.1: 99 percent / (+)-10-camphorsulfonic acid / CH₂Cl₂ / 2 h / 20 °C

3.1: 30 percent / triethylsilane; boron trifluoride diethyl etherate / CH₂Cl₂ / 0 °C

4.1: 100 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 13 h / 20 °C

5.1: 97 percent / TMSBr / CH₂Cl₂ / 24 h / -30 - 0 °C

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

7.1: LiHMDS / tetrahydrofuran; hexane / 0.33 h / 20 °C

7.2: 103 mg / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

8.1: H₂O; mercury(II) acetate; n-Bu₄NI / tetrahydrofuran / 19 h / 20 °C

9.1: 325 mg / sodium borohydride / tetrahydrofuran; H₂O / 0.25 h / 0 °C

With triethylsilane; dmap; sodium tetrahydroborate; trimethylsilyl bromide; boron trifluoride diethyl etherate; mercury(II) diacetate; water; tetra-(n-butyl)ammonium iodide; Dess-Martin periodane; (+)-10-camphorsulfonic acid; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; water; 6.1: Dess-Martin oxidation / 7.2: Wittig reaction;
DOI:10.1016/j.tet.2007.06.040