5'-O-(4,4'-dimethoxytrityl)-5-methyl-2'-O-methyl-3'-C,4'-C-ethoxymethyleneuridine

Base Information

• Chemical Name: 5'-O-(4,4'-dimethoxytrityl)-5-methyl-2'-O-methyl-3'-C,4'-C-ethoxymethyleneuridine
• CAS No.: 583843-86-1
• Molecular Formula: C₃₅H₃₈N₂O₉
• Molecular Weight: 630.695

Synonyms:5'-O-(4,4'-dimethoxytrityl)-5-methyl-2'-O-methyl-3'-C,4'-C-ethoxymethyleneuridine

Chemical Property of 5'-O-(4,4'-dimethoxytrityl)-5-methyl-2'-O-methyl-3'-C,4'-C-ethoxymethyleneuridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of 5'-O-(4,4'-dimethoxytrityl)-5-methyl-2'-O-methyl-3'-C,4'-C-ethoxymethyleneuridine

There total 25 articles about 5'-O-(4,4'-dimethoxytrityl)-5-methyl-2'-O-methyl-3'-C,4'-C-ethoxymethyleneuridine 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: 81.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + (1S,6R,8R,9R)-1-hydroxy-6-hydroxymethyl-9-methoxy-8-(thymin-1-yl)-4,7-dioxabicyclo[4.3.0]nonane (457068-13-2) → 5'-O-(4,4'-dimethoxytrityl)-5-methyl-2'-O-methyl-3'-C,4'-C-ethoxymethyleneuridine (583843-86-1)

Guidance literature:

With pyridine; at 60 ℃; for 3.5h;

Reference yield:

3-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose (879546-87-9) → 5'-O-(4,4'-dimethoxytrityl)-5-methyl-2'-O-methyl-3'-C,4'-C-ethoxymethyleneuridine (583843-86-1)

Guidance literature:

Multi-step reaction with 14 steps

1: 54 percent / sodium hydride / dimethylformamide / 1.5 h / 20 °C

2: 92 percent / Et₃N; DMAP / CH₂Cl₂ / 12 h / 20 °C

3: 25 percent / borane-1,4-oxathiane / 0 °C

4: 98 percent / H₂SO₄; acetic acid / 6 h / 20 °C

5: 95 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / 1,2-dichloro-ethane / 9 h / Heating

6: 87 percent / MeNH₂ / tetrahydrofuran; H₂O / 2 h / 0 °C

7: 90 percent / p-TsOH*H₂O / CH₂Cl₂ / 3 h / 0 °C

8: 87 percent / NaOH / tetrahydrofuran; methanol; H₂O / 1.5 h / 0 - 20 °C

9: 73 percent / sodium hexamethyldisilazide / tetrahydrofuran / 6 h / Heating

10: 85 percent / MeOH; p-TsOH*H₂O / tetrahydrofuran / 1 h / 0 °C

11: 90 percent / DBU / dimethylformamide / 0.75 h / 0 °C

12: 86 percent / sodium hydride / dimethylformamide / 1 h / 20 °C

13: 39 percent / cyclohexene / Pd(OH)2/C / ethanol / 7 h / Heating

14: 77 percent / pyridine; DMAP / 2.5 h / 50 °C

With pyridine; methanol; dmap; sodium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; borane-1,4-oxathiane; sulfuric acid; sodium hexamethyldisilazane; sodium hydride; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; methylamine; cyclohexene; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jo051187l

Reference yield:

3,5-di-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose (879546-88-0) → 5'-O-(4,4'-dimethoxytrityl)-5-methyl-2'-O-methyl-3'-C,4'-C-ethoxymethyleneuridine (583843-86-1)

Guidance literature:

Multi-step reaction with 13 steps

1: 92 percent / Et₃N; DMAP / CH₂Cl₂ / 12 h / 20 °C

2: 25 percent / borane-1,4-oxathiane / 0 °C

3: 98 percent / H₂SO₄; acetic acid / 6 h / 20 °C

4: 95 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / 1,2-dichloro-ethane / 9 h / Heating

5: 87 percent / MeNH₂ / tetrahydrofuran; H₂O / 2 h / 0 °C

6: 90 percent / p-TsOH*H₂O / CH₂Cl₂ / 3 h / 0 °C

7: 87 percent / NaOH / tetrahydrofuran; methanol; H₂O / 1.5 h / 0 - 20 °C

8: 73 percent / sodium hexamethyldisilazide / tetrahydrofuran / 6 h / Heating

9: 85 percent / MeOH; p-TsOH*H₂O / tetrahydrofuran / 1 h / 0 °C

10: 90 percent / DBU / dimethylformamide / 0.75 h / 0 °C

11: 86 percent / sodium hydride / dimethylformamide / 1 h / 20 °C

12: 39 percent / cyclohexene / Pd(OH)2/C / ethanol / 7 h / Heating

13: 77 percent / pyridine; DMAP / 2.5 h / 50 °C

With pyridine; methanol; dmap; sodium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; borane-1,4-oxathiane; sulfuric acid; sodium hexamethyldisilazane; sodium hydride; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; methylamine; cyclohexene; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jo051187l

upstream raw materials:

4,4'-dimethoxytrityl chloride

(1S,6R,8R,9R)-1-hydroxy-6-hydroxymethyl-9-methoxy-8-(thymin-1-yl)-4,7-dioxabicyclo[4.3.0]nonane

3-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose

3,5-di-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose

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