benzhydryl (1S,5R,6S)-1-(2-azidoethyl)-2-(1,3,4-thiadiazol-2-yl)thiomethyl-6-<(1R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate

Base Information

• Chemical Name: benzhydryl (1S,5R,6S)-1-(2-azidoethyl)-2-(1,3,4-thiadiazol-2-yl)thiomethyl-6-<(1R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate
• CAS No.: 220430-20-6
• Molecular Formula: C₃₃H₄₀N₆O₄S₂Si
• Molecular Weight: 676.936
• Mol file: 220430-20-6.mol

Synonyms:

Chemical Property of benzhydryl (1S,5R,6S)-1-(2-azidoethyl)-2-(1,3,4-thiadiazol-2-yl)thiomethyl-6-<(1R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzhydryl (1S,5R,6S)-1-(2-azidoethyl)-2-(1,3,4-thiadiazol-2-yl)thiomethyl-6-<(1R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate

There total 1 articles about benzhydryl (1S,5R,6S)-1-(2-azidoethyl)-2-(1,3,4-thiadiazol-2-yl)thiomethyl-6-<(1R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate 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:

(4S,5R,6S)-4-(2-Hydroxy-ethyl)-7-oxo-3-([1,3,4]thiadiazol-2-ylsulfanylmethyl)-6-((R)-1-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid benzhydryl ester (220430-46-6) → benzhydryl (1S,5R,6S)-1-(2-azidoethyl)-2-(1,3,4-thiadiazol-2-yl)thiomethyl-6-<(1R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate (220430-20-6)

Guidance literature:

With tris-(2-chloro-ethyl)-amine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 0 ℃; for 1h; Yield given;

DOI:10.3987/COM-98-8302

Reference yield: 40.0%

di-tert-butyl dicarbonate (24424-99-5) + benzhydryl (1S,5R,6S)-1-(2-azidoethyl)-2-(1,3,4-thiadiazol-2-yl)thiomethyl-6-<(1R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate (220430-20-6) → benzhydryl (1S,5R,6S)-1-(2-tert-butoxycarbonylaminoethyl)-2-(1,3,4-thiadiazol-2-yl)thiomethyl-6-<(1R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate (220430-21-7)

Guidance literature:

With trimethylphosphane; In tetrahydrofuran; water; for 15h; Ambient temperature;

DOI:10.3987/COM-98-8302

Reference yield:

benzhydryl (1S,5R,6S)-1-(2-azidoethyl)-2-(1,3,4-thiadiazol-2-yl)thiomethyl-6-<(1R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate (220430-20-6) → (4S,5R,6S)-4-(2-tert-Butoxycarbonylamino-ethyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-3-([1,3,4]thiadiazol-2-ylsulfanylmethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid benzhydryl ester (220430-47-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 40 percent / trimethylphosphine / tetrahydrofuran; H₂O / 15 h / Ambient temperature

2: 50 percent / AcOH, tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 0 °C

With tetrabutyl ammonium fluoride; acetic acid; trimethylphosphane; In tetrahydrofuran; water;

DOI:10.3987/COM-98-8302

upstream raw materials:

(4S,5R,6S)-4-(2-Hydroxy-ethyl)-7-oxo-3-([1,3,4]thiadiazol-2-ylsulfanylmethyl)-6-((R)-1-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid benzhydryl ester

Downstream raw materials:

benzhydryl (1S,5R,6S)-1-(2-tert-butoxycarbonylaminoethyl)-2-(1,3,4-thiadiazol-2-yl)thiomethyl-6-<(1R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate

(4S,5R,6S)-4-(2-tert-Butoxycarbonylamino-ethyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-3-([1,3,4]thiadiazol-2-ylsulfanylmethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid benzhydryl ester