[(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

Base Information

• Chemical Name: [(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
• CAS No.: 321866-63-1
• Molecular Formula: C₃₆H₄₉N₃O₆S
• Molecular Weight: 651.868

Synonyms:[(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

Chemical Property of [(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

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of [(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

There total 10 articles about [(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 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:

di-tert-butyl dicarbonate (24424-99-5) + (2R,3S,4S)-4-Amino-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 → [(1S,2S,3R)-3-Dibenzylcarbamoyl-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-2-methyl-butyl]-carbamic acid tert-butyl ester (321866-63-1)

Guidance literature:

With sodium hydrogencarbonate; In water; at 20 ℃; for 3h;

DOI:10.1021/ol006679t

Reference yield:

N,N-bis(phenylmethyl)-propionamide (35929-26-1) → [(1S,2S,3R)-3-Dibenzylcarbamoyl-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-2-methyl-butyl]-carbamic acid tert-butyl ester (321866-63-1)

Guidance literature:

Multi-step reaction with 4 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

3.1: SnCl₂*2H₂O / dioxane; H₂O / 20 °C

4.1: NaHCO₃ / H₂O / 3 h / 20 °C

With n-butyllithium; 2,4,6-Triisopropylbenzenesulfonyl azide; potassium hexamethylsilazane; sodium hydrogencarbonate; acetic acid; diisopropylamine; tin(ll) chloride; In tetrahydrofuran; 1,4-dioxane; hexane; water; toluene; 1.1: Michael addition;

DOI:10.1021/ol006679t

Reference yield:

(R)-10-camphorsulfonic acid (35963-20-3,61380-66-3) → [(1S,2S,3R)-3-Dibenzylcarbamoyl-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-2-methyl-butyl]-carbamic acid tert-butyl ester (321866-63-1)

Guidance literature:

Multi-step reaction with 8 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

7.1: SnCl₂*2H₂O / dioxane; H₂O / 20 °C

8.1: NaHCO₃ / H₂O / 3 h / 20 °C

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

DOI:10.1021/ol006679t

upstream raw materials:

di-tert-butyl dicarbonate

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:

(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

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