N-{9-[(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-(2-hydroxy-ethoxy)-methyl]-9H-purin-6-yl}-benzamide

Base Information

• Chemical Name: N-{9-[(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-(2-hydroxy-ethoxy)-methyl]-9H-purin-6-yl}-benzamide
• CAS No.: 121885-23-2
• Molecular Formula: C₂₀H₂₃N₅O₅
• Molecular Weight: 413.433
• Mol file: 121885-23-2.mol

Synonyms:N-{9-[(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-(2-hydroxy-ethoxy)-methyl]-9H-purin-6-yl}-benzamide

Chemical Property of N-{9-[(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-(2-hydroxy-ethoxy)-methyl]-9H-purin-6-yl}-benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{9-[(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-(2-hydroxy-ethoxy)-methyl]-9H-purin-6-yl}-benzamide

There total 7 articles about N-{9-[(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-(2-hydroxy-ethoxy)-methyl]-9H-purin-6-yl}-benzamide 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: 85.0%

N-{9-[(1R,2R)-2,3-Dihydroxy-1-(2-hydroxy-ethoxy)-propyl]-9H-purin-6-yl}-benzamide (114406-06-3) + acetone (67-64-1) → N-{9-[(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-(2-hydroxy-ethoxy)-methyl]-9H-purin-6-yl}-benzamide (121885-23-2)

Guidance literature:

With toluene-4-sulfonic acid; 2,2-dimethoxy-propane; for 1.66667h; Ambient temperature;

DOI:10.1016/S0040-4039(00)96433-5

Reference yield:

D-Ribose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) → N-{9-[(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-(2-hydroxy-ethoxy)-methyl]-9H-purin-6-yl}-benzamide (121885-23-2)

Guidance literature:

Multi-step reaction with 7 steps

2: 37 percent / bis(p-nitrophenyl)phosphate / tetrahydrothiophene 1,1-dioxide / 0.75 h / 130 °C / 100 Torr

3: 58 percent / trifluoroacetic acid / tetrahydrofuran; H₂O / 21 h / 30 °C

4: sodium periodate / H₂O; methanol / 4.5 h / Ambient temperature

5: sodium borohydride / ethanol / 1 h / -20 °C

6: NaOH / methanol / 0.33 h / 0 °C

7: 85 percent / 2,2-dimethoxypropane, TsOH / 1.67 h / Ambient temperature

With sodium hydroxide; sodium tetrahydroborate; sodium periodate; Bis(p-nitrophenyl) phosphate; toluene-4-sulfonic acid; 2,2-dimethoxy-propane; trifluoroacetic acid; In tetrahydrofuran; sulfolane; methanol; ethanol; water;

DOI:10.1016/S0040-4039(00)96433-5

Reference yield:

1,2-di-O-benzoyl-3,4-O-isopropylidene-β-D-ribopyranose (114406-04-1) → N-{9-[(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-(2-hydroxy-ethoxy)-methyl]-9H-purin-6-yl}-benzamide (121885-23-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 37 percent / bis(p-nitrophenyl)phosphate / tetrahydrothiophene 1,1-dioxide / 0.75 h / 130 °C / 100 Torr

2: 58 percent / trifluoroacetic acid / tetrahydrofuran; H₂O / 21 h / 30 °C

3: sodium periodate / H₂O; methanol / 4.5 h / Ambient temperature

4: sodium borohydride / ethanol / 1 h / -20 °C

5: NaOH / methanol / 0.33 h / 0 °C

6: 85 percent / 2,2-dimethoxypropane, TsOH / 1.67 h / Ambient temperature

With sodium hydroxide; sodium tetrahydroborate; sodium periodate; Bis(p-nitrophenyl) phosphate; toluene-4-sulfonic acid; 2,2-dimethoxy-propane; trifluoroacetic acid; In tetrahydrofuran; sulfolane; methanol; ethanol; water;

DOI:10.1016/S0040-4039(00)96433-5

upstream raw materials:

N-{9-[(1R,2R)-2,3-Dihydroxy-1-(2-hydroxy-ethoxy)-propyl]-9H-purin-6-yl}-benzamide

acetone

D-Ribose

1,2-di-O-benzoyl-3,4-O-isopropylidene-β-D-ribopyranose

Downstream raw materials:

Methanesulfonic acid (2R,3R)-3-allyloxy-3-(6-benzoylamino-purin-9-yl)-2-hydroxy-propyl ester

N-{9-[(R)-Allyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-9H-purin-6-yl}-benzamide

N-[9-((1R,2R)-1-Allyloxy-2,3-dihydroxy-propyl)-9H-purin-6-yl]-benzamide

N-[9-((R)-Allyloxy-(S)-oxiranyl-methyl)-9H-purin-6-yl]-benzamide