Benzyl (1R,2S,4S)-2λ⁴-thia-3-azabicyclo[2.2.2]oct-5-ene-3-carboxylate 2-oxide

Base Information

• Chemical Name: Benzyl (1R,2S,4S)-2λ⁴-thia-3-azabicyclo[2.2.2]oct-5-ene-3-carboxylate 2-oxide
• CAS No.: 287205-61-2
• Molecular Formula: C₁₄H₁₅NO₃S
• Molecular Weight: 277.344
• Mol file: 287205-61-2.mol

Synonyms:Benzyl (1R,2S,4S)-2λ⁴-thia-3-azabicyclo[2.2.2]oct-5-ene-3-carboxylate 2-oxide

Chemical Property of Benzyl (1R,2S,4S)-2λ⁴-thia-3-azabicyclo[2.2.2]oct-5-ene-3-carboxylate 2-oxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl (1R,2S,4S)-2λ⁴-thia-3-azabicyclo[2.2.2]oct-5-ene-3-carboxylate 2-oxide

There total 4 articles about Benzyl (1R,2S,4S)-2λ⁴-thia-3-azabicyclo[2.2.2]oct-5-ene-3-carboxylate 2-oxide 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:

N-sulfinyl benzyl carbamate (86120-34-5) + cyclohexa-1,3-diene (1165952-91-9) → (1R,2R,4S)-2-Oxo-2λ4-thia-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid benzyl ester + Benzyl (1R,2S,4S)-2λ4-thia-3-azabicyclo[2.2.2]oct-5-ene-3-carboxylate 2-oxide (287205-61-2)

Guidance literature:

With Ti(IV) complex (TADDOL-based ligand); In dichloromethane; toluene; at -55 ℃; for 20h;

DOI:10.1016/S0040-4039(00)00480-9

Reference yield:

N-sulfinyl benzyl carbamate (86120-34-5) + cyclohexa-1,3-diene (1165952-91-9) → Benzyl (1R,2S,4S)-2λ4-thia-3-azabicyclo[2.2.2]oct-5-ene-3-carboxylate 2-oxide (287205-61-2) + benzyl (1S,2R,4R)-2λ4-thia-3-azabicyclo[2.2.2]oct-5-ene-3-carboxylate 2-oxide + 2-oxo-2λ4-thia-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid benzyl ester

Guidance literature:

C₂₁H₂₂N₂O₂ chiral bis(oxazoline)-Cu(OTf)2; In dichloromethane; at -55 ℃; for 22h; Title compound not separated from byproducts;

DOI:10.1016/S0957-4166(01)00525-0

Reference yield:

N-sulfinyl benzyl carbamate (86120-34-5) + cyclohexa-1,3-diene (1165952-91-9) → Benzyl (1R,2S,4S)-2λ4-thia-3-azabicyclo[2.2.2]oct-5-ene-3-carboxylate 2-oxide (287205-61-2) + benzyl (1S,2R,4R)-2λ4-thia-3-azabicyclo[2.2.2]oct-5-ene-3-carboxylate 2-oxide + (1S,2S,4R)-2-Oxo-2λ4-thia-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid benzyl ester

Guidance literature:

With chiral Ti(IV) complex; In dichloromethane; toluene; at -68 ℃; for 18h; Title compound not separated from byproducts;

DOI:10.1016/S0957-4166(02)00661-4

upstream raw materials:

N-sulfinyl benzyl carbamate

cyclohexa-1,3-diene

Downstream raw materials:

benzyl (1S,2R)-(2-hydroxycyclohex-3-en-1-yl)carbamate

(S)-benzyl cyclohex-3-en-1-ylcarbamate

((1S,4R)-4-Benzenesulfinyl-cyclohex-2-enyl)-carbamic acid benzyl ester