Acetic acid (3S,4S)-3,5-bis-benzyloxy-1-(2,4-bis-benzyloxy-pyrimidin-5-yl)-4-(4-methoxy-benzyloxy)-pentyl ester

Base Information

• Chemical Name: Acetic acid (3S,4S)-3,5-bis-benzyloxy-1-(2,4-bis-benzyloxy-pyrimidin-5-yl)-4-(4-methoxy-benzyloxy)-pentyl ester
• CAS No.: 232939-43-4
• Molecular Formula: C₄₇H₄₈N₂O₈
• Molecular Weight: 768.907
• Mol file: 232939-43-4.mol

Synonyms:Acetic acid (3S,4S)-3,5-bis-benzyloxy-1-(2,4-bis-benzyloxy-pyrimidin-5-yl)-4-(4-methoxy-benzyloxy)-pentyl ester

Chemical Property of Acetic acid (3S,4S)-3,5-bis-benzyloxy-1-(2,4-bis-benzyloxy-pyrimidin-5-yl)-4-(4-methoxy-benzyloxy)-pentyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (3S,4S)-3,5-bis-benzyloxy-1-(2,4-bis-benzyloxy-pyrimidin-5-yl)-4-(4-methoxy-benzyloxy)-pentyl ester

There total 12 articles about Acetic acid (3S,4S)-3,5-bis-benzyloxy-1-(2,4-bis-benzyloxy-pyrimidin-5-yl)-4-(4-methoxy-benzyloxy)-pentyl 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: 93.0%

acetic anhydride (108-24-7) + (3S,4S)-3,5-Bis-benzyloxy-1-(2,4-bis-benzyloxy-pyrimidin-5-yl)-4-(4-methoxy-benzyloxy)-pentan-1-ol (232939-33-2) → Acetic acid (3S,4S)-3,5-bis-benzyloxy-1-(2,4-bis-benzyloxy-pyrimidin-5-yl)-4-(4-methoxy-benzyloxy)-pentyl ester (232939-43-4)

Guidance literature:

With pyridine; dmap; Ambient temperature;

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

Reference yield:

methyl 3,5-di-O-benzyl-2-deoxy-D-ribofuranoside (132487-16-2) → Acetic acid (3S,4S)-3,5-bis-benzyloxy-1-(2,4-bis-benzyloxy-pyrimidin-5-yl)-4-(4-methoxy-benzyloxy)-pentyl ester (232939-43-4)

Guidance literature:

Multi-step reaction with 10 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

With pyridine; methanol; dmap; sodium tetrahydroborate; oxalyl dichloride; 2,2,6,6-tetramethylpiperidinyl-lithium; water; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In ethanol; dichloromethane; N,N-dimethyl-formamide;

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

Reference yield:

3,5-di-O-benzyl-2-deoxy-D-ribofuranose (6160-50-5) → Acetic acid (3S,4S)-3,5-bis-benzyloxy-1-(2,4-bis-benzyloxy-pyrimidin-5-yl)-4-(4-methoxy-benzyloxy)-pentyl ester (232939-43-4)

Guidance literature:

Multi-step reaction with 9 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

With pyridine; methanol; dmap; sodium tetrahydroborate; oxalyl dichloride; 2,2,6,6-tetramethylpiperidinyl-lithium; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In ethanol; dichloromethane; N,N-dimethyl-formamide;

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

upstream raw materials:

acetic anhydride

(3S,4S)-3,5-Bis-benzyloxy-1-(2,4-bis-benzyloxy-pyrimidin-5-yl)-4-(4-methoxy-benzyloxy)-pentan-1-ol

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

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

Downstream raw materials:

Acetic acid (3S,4R)-4-azido-3,5-bis-benzyloxy-1-(2,4-bis-benzyloxy-pyrimidin-5-yl)-pentyl ester

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

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

(3S,4R)-4-Azido-3,5-bis-benzyloxy-1-(2,4-bis-benzyloxy-pyrimidin-5-yl)-pentan-1-one