4-<2-<(2S,4S)-4-benzoyloxy-6-methoxy-3,4,5,6-tetrahydro-2H-pyran-2-yl>-1-ene-ethyl>-3-pyridine carboxamide

Base Information

• Chemical Name: 4-<2-<(2S,4S)-4-benzoyloxy-6-methoxy-3,4,5,6-tetrahydro-2H-pyran-2-yl>-1-ene-ethyl>-3-pyridine carboxamide
• CAS No.: 146501-66-8
• Molecular Formula: C₂₁H₂₂N₂O₅
• Molecular Weight: 382.416
• Mol file: 146501-66-8.mol

Synonyms:4-<2-<(2S,4S)-4-benzoyloxy-6-methoxy-3,4,5,6-tetrahydro-2H-pyran-2-yl>-1-ene-ethyl>-3-pyridine carboxamide

Chemical Property of 4-<2-<(2S,4S)-4-benzoyloxy-6-methoxy-3,4,5,6-tetrahydro-2H-pyran-2-yl>-1-ene-ethyl>-3-pyridine carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-<2-<(2S,4S)-4-benzoyloxy-6-methoxy-3,4,5,6-tetrahydro-2H-pyran-2-yl>-1-ene-ethyl>-3-pyridine carboxamide

There total 5 articles about 4-<2-<(2S,4S)-4-benzoyloxy-6-methoxy-3,4,5,6-tetrahydro-2H-pyran-2-yl>-1-ene-ethyl>-3-pyridine carboxamide 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:

3-cyano-4-methylpyridine (5444-01-9) + Benzoic acid (2S,4S,6R)-2-formyl-6-methoxy-tetrahydro-pyran-4-yl ester (93039-20-4,93039-21-5) → 4-<2-<(2R,4S)-4-benzoyloxy-6-methoxy-3,4,5,6-tetrahydro-2H-pyran-2-yl>-1-ene-ethyl>-3-pyridine carboxamide (146501-67-9) + 4-<2-<(2S,4S)-4-benzoyloxy-6-methoxy-3,4,5,6-tetrahydro-2H-pyran-2-yl>-1-ene-ethyl>-3-pyridine carboxamide (146501-66-8)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1) DMSO, room temp., 15 min, 2) DMSO, room temp., 20 min;

DOI:10.1016/S0040-4020(01)80508-1

Reference yield:

(1R,3S,5S)-6,8-dioxabicyclo[3.2.1]octan-3-ol (14241-58-8) → 4-<2-<(2S,4S)-4-benzoyloxy-6-methoxy-3,4,5,6-tetrahydro-2H-pyran-2-yl>-1-ene-ethyl>-3-pyridine carboxamide (146501-66-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / pyridine, DMAP / 12 h / Ambient temperature

2: 12 percent / Amberlite IR H(+) / 6 h / 30 °C

3: 1) (COCl)2, DMSO / 1) CH₂Cl₂, -60 deg C, 15 min, 2) to room temp.

4: 1) NaH / 1) DMSO, room temp., 15 min, 2) DMSO, room temp., 20 min

With pyridine; dmap; oxalyl dichloride; Amberlite IR H(+); sodium hydride; dimethyl sulfoxide;

DOI:10.1016/S0040-4020(01)80508-1

Reference yield:

benzoyl chloride (98-88-4) → 4-<2-<(2S,4S)-4-benzoyloxy-6-methoxy-3,4,5,6-tetrahydro-2H-pyran-2-yl>-1-ene-ethyl>-3-pyridine carboxamide (146501-66-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / pyridine, DMAP / 12 h / Ambient temperature

2: 12 percent / Amberlite IR H(+) / 6 h / 30 °C

3: 1) (COCl)2, DMSO / 1) CH₂Cl₂, -60 deg C, 15 min, 2) to room temp.

4: 1) NaH / 1) DMSO, room temp., 15 min, 2) DMSO, room temp., 20 min

With pyridine; dmap; oxalyl dichloride; Amberlite IR H(+); sodium hydride; dimethyl sulfoxide;

DOI:10.1016/S0040-4020(01)80508-1

upstream raw materials:

3-cyano-4-methylpyridine

Benzoic acid (2S,4S,6R)-2-formyl-6-methoxy-tetrahydro-pyran-4-yl ester

(1R,3S,5S)-6,8-dioxabicyclo[3.2.1]octan-3-ol

benzoyl chloride