(2R,3R)-5-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2,3-dimethyl-5-oxo-pentanoic acid dibenzylamide

Base Information

• Chemical Name: (2R,3R)-5-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2,3-dimethyl-5-oxo-pentanoic acid dibenzylamide
• CAS No.: 321866-58-4
• Molecular Formula: C₃₁H₄₀N₂O₄S
• Molecular Weight: 536.736
• Mol file: 321866-58-4.mol

Synonyms:(2R,3R)-5-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2,3-dimethyl-5-oxo-pentanoic acid dibenzylamide

Chemical Property of (2R,3R)-5-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2,3-dimethyl-5-oxo-pentanoic acid dibenzylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-5-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2,3-dimethyl-5-oxo-pentanoic acid dibenzylamide

There total 6 articles about (2R,3R)-5-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2,3-dimethyl-5-oxo-pentanoic acid dibenzylamide 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: 72.0%

N,N-bis(phenylmethyl)-propionamide (35929-26-1) + (E)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)but-2-en-1-one (94594-81-7) → (2S,3S)-5-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2,3-dimethyl-5-oxo-pentanoic acid dibenzylamide + (2R,3R)-5-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2,3-dimethyl-5-oxo-pentanoic acid dibenzylamide (321866-58-4)

Guidance literature:

N,N-bis(phenylmethyl)-propionamide; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃;

(E)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)but-2-en-1-one; In tetrahydrofuran; hexane; at -78 ℃; Further stages.;

DOI:10.1021/ol006679t

Reference yield:

(R)-10-camphorsulfonic acid (35963-20-3,61380-66-3) → (2R,3R)-5-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2,3-dimethyl-5-oxo-pentanoic acid dibenzylamide (321866-58-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: SOCl₂

2.1: NH₃ / dioxane; H₂O

3.1: 100 percent / NaBH₄ / methanol; H₂O

4.1: 90 percent / NaH / toluene; various solvent(s) / 20 °C

5.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / -78 °C

5.2: 72 percent / tetrahydrofuran; hexane / -78 °C

With sodium tetrahydroborate; n-butyllithium; thionyl chloride; ammonia; sodium hydride; diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; water; toluene; 5.1: Michael addition;

DOI:10.1021/ol006679t

Reference yield:

(+)-camphorsultam (108448-77-7,124224-04-0) → (2R,3R)-5-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2,3-dimethyl-5-oxo-pentanoic acid dibenzylamide (321866-58-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 90 percent / NaH / toluene; various solvent(s) / 20 °C

2.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / -78 °C

2.2: 72 percent / tetrahydrofuran; hexane / -78 °C

With n-butyllithium; sodium hydride; diisopropylamine; In tetrahydrofuran; hexane; toluene; 2.1: Michael addition;

DOI:10.1021/ol006679t

upstream raw materials:

N,N-bis(phenylmethyl)-propionamide

(E)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)but-2-en-1-one

(R)-10-camphorsulfonic acid

(+)-camphorsultam

Downstream raw materials:

(2R,3S,4S)-4-Azido-5-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2,3-dimethyl-5-oxo-pentanoic acid dibenzylamide

(2S,3S,4R)-2-tert-Butoxycarbonylamino-4-dibenzylcarbamoyl-3-methyl-pentanoic acid methyl ester

(2S,3S,4R)-2-tert-Butoxycarbonylamino-4-dibenzylcarbamoyl-3-methyl-pentanoic acid

[(1S,2S,3R)-3-Dibenzylcarbamoyl-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-2-methyl-butyl]-carbamic acid tert-butyl ester