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

Base Information

• Chemical Name: Methanesulfonic acid (2R,3R)-3-allyloxy-3-(6-benzoylamino-purin-9-yl)-2-hydroxy-propyl ester
• CAS No.: 121886-82-6
• Molecular Formula: C₁₉H₂₁N₅O₆S
• Molecular Weight: 447.472

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about Methanesulfonic acid (2R,3R)-3-allyloxy-3-(6-benzoylamino-purin-9-yl)-2-hydroxy-propyl ester 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: 47.0%

N-[9-((1R,2R)-1-Allyloxy-2,3-dihydroxy-propyl)-9H-purin-6-yl]-benzamide (121885-25-4) + methanesulfonyl chloride (124-63-0) → Methanesulfonic acid (2R,3R)-3-allyloxy-3-(6-benzoylamino-purin-9-yl)-2-hydroxy-propyl ester (121886-82-6)

Guidance literature:

With triethylamine; In dichloromethane; N,N-dimethyl-formamide; at 0 ℃; for 0.666667h;

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) → Methanesulfonic acid (2R,3R)-3-allyloxy-3-(6-benzoylamino-purin-9-yl)-2-hydroxy-propyl ester (121886-82-6)

Guidance literature:

Multi-step reaction with 11 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

8: 76 percent / DMSO, (COCl)2, Et₃N / CH₂Cl₂

9: 33 percent / tetrahydrofuran; dimethylsulfoxide; hexamethylphosphoric acid triamide / 0.5 h / -20 °C

10: 93 percent / trifluoroacetic acid / tetrahydrofuran; H₂O / 15.5 h / Ambient temperature

11: 47 percent / Et₃N / dimethylformamide; CH₂Cl₂ / 0.67 h / 0 °C

With sodium hydroxide; sodium tetrahydroborate; sodium periodate; oxalyl dichloride; Bis(p-nitrophenyl) phosphate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 2,2-dimethoxy-propane; trifluoroacetic acid; In tetrahydrofuran; sulfolane; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

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) → Methanesulfonic acid (2R,3R)-3-allyloxy-3-(6-benzoylamino-purin-9-yl)-2-hydroxy-propyl ester (121886-82-6)

Guidance literature:

Multi-step reaction with 10 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

7: 76 percent / DMSO, (COCl)2, Et₃N / CH₂Cl₂

8: 33 percent / tetrahydrofuran; dimethylsulfoxide; hexamethylphosphoric acid triamide / 0.5 h / -20 °C

9: 93 percent / trifluoroacetic acid / tetrahydrofuran; H₂O / 15.5 h / Ambient temperature

10: 47 percent / Et₃N / dimethylformamide; CH₂Cl₂ / 0.67 h / 0 °C

With sodium hydroxide; sodium tetrahydroborate; sodium periodate; oxalyl dichloride; Bis(p-nitrophenyl) phosphate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 2,2-dimethoxy-propane; trifluoroacetic acid; In tetrahydrofuran; sulfolane; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

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

upstream raw materials:

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

methanesulfonyl chloride

D-Ribose

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

Downstream raw materials:

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

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