(1S,5R,6R)-4-phenylmethyl-4,11-diaza-6-((1(S)-ethyl-3,3-dimethyl(2,4-dioxolanyl))methyl)-9-(methoxycarbonyl)tetracyclo[8.7.0.0^1,5.0^12,17]heptadeca-9,12⁽¹³⁾,14,16-tetraene-4-carboxylate

Base Information

• Chemical Name: (1S,5R,6R)-4-phenylmethyl-4,11-diaza-6-((1(S)-ethyl-3,3-dimethyl(2,4-dioxolanyl))methyl)-9-(methoxycarbonyl)tetracyclo[8.7.0.0^1,5.0^12,17]heptadeca-9,12⁽¹³⁾,14,16-tetraene-4-carboxylate
• CAS No.: 362517-23-5
• Molecular Formula: C₃₂H₄₀N₂O₄
• Molecular Weight: 516.681

Synonyms:(1S,5R,6R)-4-phenylmethyl-4,11-diaza-6-((1(S)-ethyl-3,3-dimethyl(2,4-dioxolanyl))methyl)-9-(methoxycarbonyl)tetracyclo[8.7.0.0^1,5.0^12,17]heptadeca-9,12⁽¹³⁾,14,16-tetraene-4-carboxylate

Chemical Property of (1S,5R,6R)-4-phenylmethyl-4,11-diaza-6-((1(S)-ethyl-3,3-dimethyl(2,4-dioxolanyl))methyl)-9-(methoxycarbonyl)tetracyclo[8.7.0.0^1,5.0^12,17]heptadeca-9,12⁽¹³⁾,14,16-tetraene-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (1S,5R,6R)-4-phenylmethyl-4,11-diaza-6-((1(S)-ethyl-3,3-dimethyl(2,4-dioxolanyl))methyl)-9-(methoxycarbonyl)tetracyclo[8.7.0.0^1,5.0^12,17]heptadeca-9,12⁽¹³⁾,14,16-tetraene-4-carboxylate

There total 11 articles about (1S,5R,6R)-4-phenylmethyl-4,11-diaza-6-((1(S)-ethyl-3,3-dimethyl(2,4-dioxolanyl))methyl)-9-(methoxycarbonyl)tetracyclo[8.7.0.0^1,5.0^12,17]heptadeca-9,12⁽¹³⁾,14,16-tetraene-4-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:

(3aR,4S,5S,11bS)-methyl 2,3,3a,4,5,7-hexahydro-4-[(2S)-2-ethyl-2,3-(isopropylidenedioxy)propyl]-1H-pyrrolo[2,3-d]carbazole-5-hydroxymethyl-6-carboxylate (362517-11-1) → (1S,5R,6R)-4-phenylmethyl-4,11-diaza-6-((1(S)-ethyl-3,3-dimethyl(2,4-dioxolanyl))methyl)-9-(methoxycarbonyl)tetracyclo[8.7.0.01,5.012,17]heptadeca-9,12(13),14,16-tetraene-4-carboxylate (362517-23-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 6.940 g / sodium hydrogencarbonate / acetone; H₂O / 0.33 h / 0 °C

2.1: p-toluenesulfonic anhydride; triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 5 h

2.2: 92.3 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 24 h

3.1: thiocresol / 2 h / 110 °C

3.2: tributyltin hydride; 2,2'-diazobisisobutyronitrile / toluene / 24 h / Heating

3.3: H₂; triethylamine / Pd(OH)2/C / ethyl acetate / 1 h

4.1: 1.231 g / triethylamine; potassium carbonate / acetone / 15 h

With dmap; p-toluenesulfonylanhydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; para-thiocresol; In dichloromethane; water; acetone;

DOI:10.1021/jo000250y

Reference yield:

(3aR,4S,5S,11bS)-dimethyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-[(2R)-2-ethyl-2,3-(dihydroxy)propyl]-1H-pyrrolo[2,3-d]carbazole-5,6-dicarboxylate (362517-04-2) → (1S,5R,6R)-4-phenylmethyl-4,11-diaza-6-((1(S)-ethyl-3,3-dimethyl(2,4-dioxolanyl))methyl)-9-(methoxycarbonyl)tetracyclo[8.7.0.01,5.012,17]heptadeca-9,12(13),14,16-tetraene-4-carboxylate (362517-23-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 98.7 percent / triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 5 h

2.1: 96.3 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 8 h

3.1: 13.6 percent / sulfuric acid/silica gel; water / dioxane / 0.17 h

4.1: 81.7 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 0 - 20 °C

5.1: ammonium formate / Pd/C / methanol; ethyl acetate / 2 h / Heating

6.1: 6.940 g / sodium hydrogencarbonate / acetone; H₂O / 0.33 h / 0 °C

7.1: p-toluenesulfonic anhydride; triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 5 h

7.2: 92.3 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 24 h

8.1: thiocresol / 2 h / 110 °C

8.2: tributyltin hydride; 2,2'-diazobisisobutyronitrile / toluene / 24 h / Heating

8.3: H₂; triethylamine / Pd(OH)2/C / ethyl acetate / 1 h

9.1: 1.231 g / triethylamine; potassium carbonate / acetone / 15 h

With dmap; sulfuric acid; p-toluenesulfonylanhydride; water; ammonium formate; silica gel; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; para-thiocresol; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; ethyl acetate; acetone;

DOI:10.1021/jo000250y

Reference yield:

(3aR,4S,5S,11bS)-dimethyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-[(2R)-2-ethyl-2,3-epoxypropyl]-1H-pyrrolo[2,3-d]carbazole-5,6-dicarboxylate (362517-06-4) → (1S,5R,6R)-4-phenylmethyl-4,11-diaza-6-((1(S)-ethyl-3,3-dimethyl(2,4-dioxolanyl))methyl)-9-(methoxycarbonyl)tetracyclo[8.7.0.01,5.012,17]heptadeca-9,12(13),14,16-tetraene-4-carboxylate (362517-23-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 13.6 percent / sulfuric acid/silica gel; water / dioxane / 0.17 h

2.1: 81.7 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 0 - 20 °C

3.1: ammonium formate / Pd/C / methanol; ethyl acetate / 2 h / Heating

4.1: 6.940 g / sodium hydrogencarbonate / acetone; H₂O / 0.33 h / 0 °C

5.1: p-toluenesulfonic anhydride; triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 5 h

5.2: 92.3 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 24 h

6.1: thiocresol / 2 h / 110 °C

6.2: tributyltin hydride; 2,2'-diazobisisobutyronitrile / toluene / 24 h / Heating

6.3: H₂; triethylamine / Pd(OH)2/C / ethyl acetate / 1 h

7.1: 1.231 g / triethylamine; potassium carbonate / acetone / 15 h

With dmap; sulfuric acid; p-toluenesulfonylanhydride; water; ammonium formate; silica gel; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; para-thiocresol; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; ethyl acetate; acetone;

DOI:10.1021/jo000250y

upstream raw materials:

benzyl bromide

(1S,5R,6R)-4,11-diaza-6-((1(S)-ethyl-3,3-dimethyl(2,4-dioxolanyl))methyl)-9-(methoxycarbonyl)tetracyclo[8.7.0.0^1,5.0^12,17]heptadeca-9,12⁽¹³⁾,14,16-tetraene-4-carboxylate

(3aR,4S,5S,11bS)-methyl 2,3,3a,4,5,7-hexahydro-4-[(2S)-2-ethyl-2,3-(isopropylidenedioxy)propyl]-1H-pyrrolo[2,3-d]carbazole-5-hydroxymethyl-6-carboxylate

(3aR,4S,5S,11bS)-dimethyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-[(2R)-2-ethyl-2,3-epoxypropyl]-1H-pyrrolo[2,3-d]carbazole-5,6-dicarboxylate

Downstream raw materials:

(2S,5R)-methyl 7,17-diaza-5-(2(R)-ethyl-2,3-epoxypropyl)-7-benzyltricyclo[8.7.0.0^11,16]heptadeca-1⁽¹⁰⁾,6,11⁽¹⁶⁾,12,14-pentaene-2-(10-vindolinyl)-2-carboxylate

C₅₄H₆₆N₄O₉

C₅₄H₆₈N₄O₁₀

C₅₄H₆₈N₄O₁₀

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