diethyl (4S)-2-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)-1,4-dihydro-6-methyl-4-phenylpyridine-3,5-dicarboxylate

Base Information

• Chemical Name: diethyl (4S)-2-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)-1,4-dihydro-6-methyl-4-phenylpyridine-3,5-dicarboxylate
• CAS No.: 421554-04-3
• Molecular Formula: C₄₄H₄₇NO₈
• Molecular Weight: 717.859
• Mol file: 421554-04-3.mol

Synonyms:diethyl (4S)-2-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)-1,4-dihydro-6-methyl-4-phenylpyridine-3,5-dicarboxylate

Chemical Property of diethyl (4S)-2-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)-1,4-dihydro-6-methyl-4-phenylpyridine-3,5-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diethyl (4S)-2-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)-1,4-dihydro-6-methyl-4-phenylpyridine-3,5-dicarboxylate

There total 3 articles about diethyl (4S)-2-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)-1,4-dihydro-6-methyl-4-phenylpyridine-3,5-dicarboxylate 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: 49.0%

ethyl 2-benzylidene acetoacetate (620-80-4) + ethyl 3-amino-3-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)propenoate (421553-97-1) → diethyl (4R)-2-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)-6-methyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate (421554-03-2) + diethyl (4S)-2-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)-1,4-dihydro-6-methyl-4-phenylpyridine-3,5-dicarboxylate (421554-04-3)

Guidance literature:

With 4 A molecular sieve; acetic acid; In toluene; at 120 ℃; for 12h;

DOI:10.1002/1522-2675(200210)85:10<3331::AID-HLCA3331>3.0.CO;2-X

Reference yield:

2,5-anhydro-3,4,6-tri-O-benzyl-D-allononitrile (52492-43-0,52492-44-1,82267-01-4,82267-02-5,139189-60-9) → diethyl (4S)-2-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)-1,4-dihydro-6-methyl-4-phenylpyridine-3,5-dicarboxylate (421554-04-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / Zn / tetrahydrofuran / Heating

2: 43 percent / mol. sieves 4 Angstroem / dimethylformamide / 48 h / 150 °C

With 4 A molecular sieve; zinc; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1002/1522-2675(200210)85:10<3331::AID-HLCA3331>3.0.CO;2-X

Reference yield:

ethyl 3-oxo-3-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)propanoate (359017-30-4) → diethyl (4S)-2-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)-1,4-dihydro-6-methyl-4-phenylpyridine-3,5-dicarboxylate (421554-04-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / AcONH₄; AcOH; mol sieves 4 Angstroem / toluene / 1.5 h / 120 °C

2: 43 percent / mol. sieves 4 Angstroem / dimethylformamide / 48 h / 150 °C

With 4 A molecular sieve; ammonium acetate; acetic acid; In N,N-dimethyl-formamide; toluene;

DOI:10.1002/1522-2675(200210)85:10<3331::AID-HLCA3331>3.0.CO;2-X

upstream raw materials:

ethyl 2-benzylidene acetoacetate

ethyl 3-amino-3-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)propenoate

2,5-anhydro-3,4,6-tri-O-benzyl-D-allononitrile

ethyl 3-oxo-3-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)propanoate