N-[9-((2S,3R,4S)-3,4-Bis-benzyloxymethyl-oxetan-2-yl)-9H-purin-6-yl]-benzamide

Base Information

• Chemical Name: N-[9-((2S,3R,4S)-3,4-Bis-benzyloxymethyl-oxetan-2-yl)-9H-purin-6-yl]-benzamide
• CAS No.: 132454-58-1
• Molecular Formula: C₃₁H₂₉N₅O₄
• Molecular Weight: 535.602
• Mol file: 132454-58-1.mol

Synonyms:

Chemical Property of N-[9-((2S,3R,4S)-3,4-Bis-benzyloxymethyl-oxetan-2-yl)-9H-purin-6-yl]-benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[9-((2S,3R,4S)-3,4-Bis-benzyloxymethyl-oxetan-2-yl)-9H-purin-6-yl]-benzamide

There total 30 articles about N-[9-((2S,3R,4S)-3,4-Bis-benzyloxymethyl-oxetan-2-yl)-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:

((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol (69832-48-0) → N-[9-((2R,3R,4S)-3,4-Bis-benzyloxymethyl-oxetan-2-yl)-9H-purin-6-yl]-benzamide (132454-58-1)

Guidance literature:

Multi-step reaction with 13 steps

1: AcOH / H₂O

2: NaIO₄ / ethanol; H₂O

3: NaBH₄ / ethanol

4: NaH / dimethylformamide

5: aq. TFA

6: Br₂, barium benzoate / H₂O; dioxane

7: pyridine / CH₂Cl₂ / -30 °C

8: 56 percent / K₂CO₃

9: hydrolyse

10: oxalyl chloride

12: decarboxylative chlorination

13: K₂CO₃

With pyridine; sodium tetrahydroborate; sodium periodate; oxalyl dichloride; bromine; sodium hydride; potassium carbonate; acetic acid; barium benzoate; trifluoroacetic acid; In 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)97210-1

Reference yield:

((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol (69832-48-0) → N-[9-((2S,3R,4S)-3,4-Bis-benzyloxymethyl-oxetan-2-yl)-9H-purin-6-yl]-benzamide (132454-58-1)

Guidance literature:

Multi-step reaction with 13 steps

1: AcOH / H₂O

2: NaIO₄ / ethanol; H₂O

3: NaBH₄ / ethanol

4: NaH / dimethylformamide

5: aq. TFA

6: Br₂, barium benzoate / H₂O; dioxane

7: pyridine / CH₂Cl₂ / -30 °C

8: 56 percent / K₂CO₃

9: hydrolyse

10: oxalyl chloride

12: decarboxylative chlorination

13: K₂CO₃

With pyridine; sodium tetrahydroborate; sodium periodate; oxalyl dichloride; bromine; sodium hydride; potassium carbonate; acetic acid; barium benzoate; trifluoroacetic acid; In 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)97210-1

Reference yield:

(R)-1-((3aR,5S,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol (26277-33-8) → N-[9-((2S,3R,4S)-3,4-Bis-benzyloxymethyl-oxetan-2-yl)-9H-purin-6-yl]-benzamide (132454-58-1)

Guidance literature:

Multi-step reaction with 12 steps

1: NaIO₄ / ethanol; H₂O

2: NaBH₄ / ethanol

3: NaH / dimethylformamide

4: aq. TFA

5: Br₂, barium benzoate / H₂O; dioxane

6: pyridine / CH₂Cl₂ / -30 °C

7: 56 percent / K₂CO₃

8: hydrolyse

9: oxalyl chloride

11: decarboxylative chlorination

12: K₂CO₃

With pyridine; sodium tetrahydroborate; sodium periodate; oxalyl dichloride; bromine; sodium hydride; potassium carbonate; barium benzoate; trifluoroacetic acid; In 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)97210-1

upstream raw materials:

(2S,3R)-2,3-Bis-benzyloxymethyl-4-chloro-oxetane

N-benzoyladenine

((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol

((3aR,5S,6R,6aR)-5-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-methanol

Downstream raw materials:

α-Oxetanocin

(-)-oxetanocin