(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

Base Information

• Chemical Name: (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
• CAS No.: 321866-62-0
• Molecular Formula: C₃₁H₃₉N₅O₄S
• Molecular Weight: 577.748

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

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Technology Process of (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

There total 8 articles about (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 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: 78.0%

(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) → (2R,3S,4S)-4-Azido-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 (321866-62-0)

Guidance literature:

With 2,4,6-Triisopropylbenzenesulfonyl azide; potassium hexamethylsilazane; acetic acid; In tetrahydrofuran; toluene; at 30 ℃; for 2h;

DOI:10.1021/ol006679t

Reference yield:

N,N-bis(phenylmethyl)-propionamide (35929-26-1) → (2R,3S,4S)-4-Azido-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 (321866-62-0)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 72 percent / tetrahydrofuran; hexane / -78 °C

2.1: 78 percent / KHMDS; 2,4,6-triisopropylbenznesulfonyl azide; acetic acid / tetrahydrofuran; toluene / 2 h / 30 °C

With n-butyllithium; 2,4,6-Triisopropylbenzenesulfonyl azide; potassium hexamethylsilazane; acetic acid; diisopropylamine; In tetrahydrofuran; hexane; toluene; 1.1: Michael addition;

DOI:10.1021/ol006679t

Reference yield:

(R)-10-camphorsulfonic acid (35963-20-3,61380-66-3) → (2R,3S,4S)-4-Azido-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 (321866-62-0)

Guidance literature:

Multi-step reaction with 6 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

6.1: 78 percent / KHMDS; 2,4,6-triisopropylbenznesulfonyl azide; acetic acid / tetrahydrofuran; toluene / 2 h / 30 °C

With sodium tetrahydroborate; n-butyllithium; thionyl chloride; 2,4,6-Triisopropylbenzenesulfonyl azide; ammonia; potassium hexamethylsilazane; sodium hydride; acetic acid; diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; water; toluene; 5.1: Michael addition;

DOI:10.1021/ol006679t

upstream raw materials:

(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

N,N-bis(phenylmethyl)-propionamide

(R)-10-camphorsulfonic acid

(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

Downstream raw materials:

[(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

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

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

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