(1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-5-(hexadecanoyl)-7-hydroxy-3-(4-N-benzoyl-5-methylcytosine-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

Base Information

• Chemical Name: (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-5-(hexadecanoyl)-7-hydroxy-3-(4-N-benzoyl-5-methylcytosine-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane
• CAS No.: 1415236-73-5
• Molecular Formula: C₅₅H₆₈N₄O₈
• Molecular Weight: 913.167
• Mol file: 1415236-73-5.mol

Synonyms:(1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-5-(hexadecanoyl)-7-hydroxy-3-(4-N-benzoyl-5-methylcytosine-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

Chemical Property of (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-5-(hexadecanoyl)-7-hydroxy-3-(4-N-benzoyl-5-methylcytosine-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-5-(hexadecanoyl)-7-hydroxy-3-(4-N-benzoyl-5-methylcytosine-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

There total 16 articles about (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-5-(hexadecanoyl)-7-hydroxy-3-(4-N-benzoyl-5-methylcytosine-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane 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:

(1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-5-(hexadecanoyl)-7-hydroxy-3-(5-methylcytosine-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane (1415236-77-9) + benzoic acid anhydride (93-97-0) → (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-5-(hexadecanoyl)-7-hydroxy-3-(4-N-benzoyl-5-methylcytosine-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane (1415236-73-5)

Guidance literature:

With pyridine; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

DOI:10.1021/jo302036h

Reference yield:

3-O-benzyl-4-C-methanesulfonoxymethyl-5-methanesulfonyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose (293751-01-6) → (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-5-(hexadecanoyl)-7-hydroxy-3-(4-N-benzoyl-5-methylcytosine-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane (1415236-73-5)

Guidance literature:

Multi-step reaction with 16 steps

1.1: trifluoroacetic acid / water / 4 h / 0 °C

2.1: pyridine / 58 h / 0 °C / Inert atmosphere

3.1: N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate / acetonitrile / 0 - 60 °C / Inert atmosphere

4.1: ammonia / methanol / 0 °C / Inert atmosphere

5.1: pyridine / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

5.2: 0 - 20 °C / Inert atmosphere

6.1: sulfuric acid / water; acetone / 3 h / Reflux

7.1: pyridine; dmap; trifluoromethylsulfonic anhydride / dichloromethane / 2 h / 0 °C / Inert atmosphere

7.2: 19 h / 80 °C / Inert atmosphere

8.1: sodium hydroxide; trimethylphosphane / water; tetrahydrofuran / 14 h / 0 - 20 °C / Inert atmosphere

9.1: 18-crown-6 ether / 1,4-dioxane / 80 °C / Inert atmosphere

10.1: ammonia / methanol / 0 °C / Inert atmosphere; Heating

11.1: pyridine / dichloromethane / 1.17 h / -70 - 0 °C / Inert atmosphere

12.1: pyridine / dichloromethane / 18 h / 20 °C / Inert atmosphere

13.1: triethylamine; 1,2,4-Triazole; trichlorophosphate / acetonitrile / 1.17 h / 0 - 2 °C / Inert atmosphere

13.2: 1 h

14.1: palladium on carbon; ammonium formate / methanol / Inert atmosphere; Reflux

15.1: pyridine / dichloromethane / 3 h / 0 °C / Inert atmosphere

16.1: pyridine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

With pyridine; 1,2,4-Triazole; dmap; N,O-bis-(trimethylsilyl)-acetamide; 18-crown-6 ether; trifluoromethylsulfonic anhydride; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; palladium on carbon; ammonia; ammonium formate; triethylamine; trifluoroacetic acid; sodium hydroxide; trichlorophosphate; trimethylphosphane; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 3.1: |Vorbrueggen Nucleoside Synthesis / 8.1: |Staudinger Azide Reduction;

DOI:10.1021/jo302036h

Reference yield:

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-5-(hexadecanoyl)-7-hydroxy-3-(4-N-benzoyl-5-methylcytosine-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane (1415236-73-5)

Guidance literature:

Multi-step reaction with 17 steps

1.1: pyridine / 20 h / 0 - 20 °C / Inert atmosphere

2.1: trifluoroacetic acid / water / 4 h / 0 °C

3.1: pyridine / 58 h / 0 °C / Inert atmosphere

4.1: N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate / acetonitrile / 0 - 60 °C / Inert atmosphere

5.1: ammonia / methanol / 0 °C / Inert atmosphere

6.1: pyridine / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

6.2: 0 - 20 °C / Inert atmosphere

7.1: sulfuric acid / water; acetone / 3 h / Reflux

8.1: pyridine; dmap; trifluoromethylsulfonic anhydride / dichloromethane / 2 h / 0 °C / Inert atmosphere

8.2: 19 h / 80 °C / Inert atmosphere

9.1: sodium hydroxide; trimethylphosphane / water; tetrahydrofuran / 14 h / 0 - 20 °C / Inert atmosphere

10.1: 18-crown-6 ether / 1,4-dioxane / 80 °C / Inert atmosphere

11.1: ammonia / methanol / 0 °C / Inert atmosphere; Heating

12.1: pyridine / dichloromethane / 1.17 h / -70 - 0 °C / Inert atmosphere

13.1: pyridine / dichloromethane / 18 h / 20 °C / Inert atmosphere

14.1: triethylamine; 1,2,4-Triazole; trichlorophosphate / acetonitrile / 1.17 h / 0 - 2 °C / Inert atmosphere

14.2: 1 h

15.1: palladium on carbon; ammonium formate / methanol / Inert atmosphere; Reflux

16.1: pyridine / dichloromethane / 3 h / 0 °C / Inert atmosphere

17.1: pyridine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

With pyridine; 1,2,4-Triazole; dmap; N,O-bis-(trimethylsilyl)-acetamide; 18-crown-6 ether; trifluoromethylsulfonic anhydride; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; palladium on carbon; ammonia; ammonium formate; triethylamine; trifluoroacetic acid; sodium hydroxide; trichlorophosphate; trimethylphosphane; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 4.1: |Vorbrueggen Nucleoside Synthesis / 9.1: |Staudinger Azide Reduction;

DOI:10.1021/jo302036h

upstream raw materials:

1-[2-azido-3-O-benzyl-2-deoxy-5-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl]thymine

(1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonyloxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

(1R,3R,4R,7S)-1-benzoyloxymethyl-7-benzyloxy-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

(1R,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

Downstream raw materials:

(1R,3R,4R,7S)-7-(2-cyanoethoxy(diisopropylamino)phosphinoxy)-1-(4,4'-dimethoxytrityloxymethyl)-5-(hexadecanoyl)-7-hydroxy-3-(4-N-benzoyl-5-methylcytosine-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane