1-[(2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(2,4-bis-benzyloxy-pyrimidin-5-yl)-pyrrolidin-1-yl]-ethanone

Base Information

• Chemical Name: 1-[(2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(2,4-bis-benzyloxy-pyrimidin-5-yl)-pyrrolidin-1-yl]-ethanone
• CAS No.: 232939-39-8
• Molecular Formula: C₃₉H₃₉N₃O₅
• Molecular Weight: 629.756
• Mol file: 232939-39-8.mol

Synonyms:

Chemical Property of 1-[(2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(2,4-bis-benzyloxy-pyrimidin-5-yl)-pyrrolidin-1-yl]-ethanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(2,4-bis-benzyloxy-pyrimidin-5-yl)-pyrrolidin-1-yl]-ethanone

There total 19 articles about 1-[(2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(2,4-bis-benzyloxy-pyrimidin-5-yl)-pyrrolidin-1-yl]-ethanone 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: 92.0%

acetic anhydride (108-24-7) + 2,4-Bis-benzyloxy-5-((2R,4S,5R)-4-benzyloxy-5-benzyloxymethyl-pyrrolidin-2-yl)-pyrimidine (232939-38-7) → 1-[(2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(2,4-bis-benzyloxy-pyrimidin-5-yl)-pyrrolidin-1-yl]-ethanone (232939-39-8)

Guidance literature:

With pyridine; dmap;

DOI:10.1016/S0040-4039(99)00854-0

Reference yield:

3,5-di-O-benzyl-2-deoxy-D-ribofuranose (6160-50-5) → 1-[(2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(2,4-bis-benzyloxy-pyrimidin-5-yl)-pyrrolidin-1-yl]-ethanone (232939-39-8)

Guidance literature:

Multi-step reaction with 16 steps

1: NaBH₄ / ethanol / 0 °C

2: 98 percent / DMAP, Et₃N / CH₂Cl₂ / Ambient temperature

3: 1) Ph₃P, DEAD / 1) benzene, 0 deg C, 2) benzene, 0 deg C, 5 h

4: 95 percent / K₂CO₃, MeOH / 3 h / Ambient temperature

5: 92 percent / NaH / dimethylformamide / 0 °C

6: 98 percent / TsOH, MeOH / CH₂Cl₂ / Ambient temperature

7: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂, -78 to 0 deg C

8: 1) lithium 2,2,6,6-tetramethylpiperidine / 1) THF, -78 deg C, 2) THF, -78 deg C

9: 93 percent / DMAP, pyridine / Ambient temperature

10: 84 percent / DDQ, H₂O / CH₂Cl₂ / Ambient temperature

11: 1) Ph₃P, DEAD, 2) diphenylphosphoryl azide / 1) THF, RT, 2) THF, RT

12: 95 percent / K₂CO₃, MeOH / Ambient temperature

13: 81 percent / MnO₂ / tetrahydrofuran / 24 h

14: 91 percent / PPh₃ / tetrahydrofuran / 18 h / Ambient temperature

15: 41 percent / NaBH₃CN, AcOH / methanol

16: 92 percent / DMAP, pyridine

With pyridine; methanol; dmap; manganese(IV) oxide; sodium tetrahydroborate; oxalyl dichloride; diphenylphosphoranyl azide; 2,2,6,6-tetramethylpiperidinyl-lithium; water; sodium hydride; sodium cyanoborohydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(99)00854-0

Reference yield:

methyl 3,5-di-O-benzyl-2-deoxy-D-ribofuranoside (132487-16-2) → 1-[(2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(2,4-bis-benzyloxy-pyrimidin-5-yl)-pyrrolidin-1-yl]-ethanone (232939-39-8)

Guidance literature:

Multi-step reaction with 17 steps

1: AcOH, H₂O / 100 °C

2: NaBH₄ / ethanol / 0 °C

3: 98 percent / DMAP, Et₃N / CH₂Cl₂ / Ambient temperature

4: 1) Ph₃P, DEAD / 1) benzene, 0 deg C, 2) benzene, 0 deg C, 5 h

5: 95 percent / K₂CO₃, MeOH / 3 h / Ambient temperature

6: 92 percent / NaH / dimethylformamide / 0 °C

7: 98 percent / TsOH, MeOH / CH₂Cl₂ / Ambient temperature

8: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂, -78 to 0 deg C

9: 1) lithium 2,2,6,6-tetramethylpiperidine / 1) THF, -78 deg C, 2) THF, -78 deg C

10: 93 percent / DMAP, pyridine / Ambient temperature

11: 84 percent / DDQ, H₂O / CH₂Cl₂ / Ambient temperature

12: 1) Ph₃P, DEAD, 2) diphenylphosphoryl azide / 1) THF, RT, 2) THF, RT

13: 95 percent / K₂CO₃, MeOH / Ambient temperature

14: 81 percent / MnO₂ / tetrahydrofuran / 24 h

15: 91 percent / PPh₃ / tetrahydrofuran / 18 h / Ambient temperature

16: 41 percent / NaBH₃CN, AcOH / methanol

17: 92 percent / DMAP, pyridine

With pyridine; methanol; dmap; manganese(IV) oxide; sodium tetrahydroborate; oxalyl dichloride; diphenylphosphoranyl azide; 2,2,6,6-tetramethylpiperidinyl-lithium; water; sodium hydride; sodium cyanoborohydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(99)00854-0

upstream raw materials:

acetic anhydride

2,4-Bis-benzyloxy-5-((2R,4S,5R)-4-benzyloxy-5-benzyloxymethyl-pyrrolidin-2-yl)-pyrimidine

3,5-di-O-benzyl-2-deoxy-D-ribofuranose

methyl 3,5-di-O-benzyl-2-deoxy-D-ribofuranoside