(2R,3S,4R,5R,6S)-2-((1H-tetrazol-1-yl)methyl)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)tetrahydro-2H-pyran-3,4,5-triol

Base Information

• Chemical Name: (2R,3S,4R,5R,6S)-2-((1H-tetrazol-1-yl)methyl)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)tetrahydro-2H-pyran-3,4,5-triol
• CAS No.: 1270018-31-9
• Molecular Formula: C₂₁H₂₀ClN₅O₅S
• Molecular Weight: 489.939
• Mol file: 1270018-31-9.mol

Synonyms:

Chemical Property of (2R,3S,4R,5R,6S)-2-((1H-tetrazol-1-yl)methyl)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)tetrahydro-2H-pyran-3,4,5-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R,5R,6S)-2-((1H-tetrazol-1-yl)methyl)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)tetrahydro-2H-pyran-3,4,5-triol

There total 6 articles about (2R,3S,4R,5R,6S)-2-((1H-tetrazol-1-yl)methyl)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)tetrahydro-2H-pyran-3,4,5-triol 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:

1H-tetrazole (288-94-8) + C27H26ClNO7S2 → (2R,3S,4R,5R,6S)-2-((1H-tetrazol-1-yl)methyl)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)tetrahydro-2H-pyran-3,4,5-triol (1270018-31-9) + (2R,3S,4R,5R,6S)-2-((2H-tetrazol-2-yl)methyl)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-tetrahydro-2H-pyran-3,4,5-triol (1270018-29-5)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 80 ℃; for 72h;

DOI:10.1016/j.bmcl.2010.11.115

Reference yield:

2-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)acetic acid (1225430-40-9) → (2R,3S,4R,5R,6S)-2-((1H-tetrazol-1-yl)methyl)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)tetrahydro-2H-pyran-3,4,5-triol (1270018-31-9) + (2R,3S,4R,5R,6S)-2-((2H-tetrazol-2-yl)methyl)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-tetrahydro-2H-pyran-3,4,5-triol (1270018-29-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 20 °C

2: Lawessons reagent / tetrahydrofuran / 85 °C

3: boron trichloride / dichloromethane / 0 °C

4: 2,6-dimethylpyridine / 15 h / 20 °C

5: triethylamine / N,N-dimethyl-formamide / 72 h / 80 °C

With Lawessons reagent; 4-methyl-morpholine; 2,6-dimethylpyridine; boron trichloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2010.11.115

Reference yield:

C48H46ClNO8 (1270017-92-9) → (2R,3S,4R,5R,6S)-2-((1H-tetrazol-1-yl)methyl)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)tetrahydro-2H-pyran-3,4,5-triol (1270018-31-9) + (2R,3S,4R,5R,6S)-2-((2H-tetrazol-2-yl)methyl)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-tetrahydro-2H-pyran-3,4,5-triol (1270018-29-5)

Guidance literature:

Multi-step reaction with 4 steps

1: Lawessons reagent / tetrahydrofuran / 85 °C

2: boron trichloride / dichloromethane / 0 °C

3: 2,6-dimethylpyridine / 15 h / 20 °C

4: triethylamine / N,N-dimethyl-formamide / 72 h / 80 °C

With Lawessons reagent; 2,6-dimethylpyridine; boron trichloride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2010.11.115

upstream raw materials:

1H-tetrazole

2-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)acetic acid

C₄₈H₄₆ClNO₈

C₄₈H₄₄ClNO₆S