benzyl 5,17-bisbenzyloxy-14(S)-benzyloxycarbonylamino-11(S)-(3-benzyloxycarbonylamino-2(R)-hydroxypropyl)-10,13-dioxo-9,12-diazatricyclo[14.3.1.12,6]-henicosa-1(19),2,4,6(21),16(20),17-hexaene-8(S)-carboxylate

Base Information

• Chemical Name: benzyl 5,17-bisbenzyloxy-14(S)-benzyloxycarbonylamino-11(S)-(3-benzyloxycarbonylamino-2(R)-hydroxypropyl)-10,13-dioxo-9,12-diazatricyclo[14.3.1.12,6]-henicosa-1(19),2,4,6(21),16(20),17-hexaene-8(S)-carboxylate
• CAS No.: 134038-87-2
• Molecular Formula: C₆₀H₅₈N₄O₁₁
• Molecular Weight: 1011.14
• Mol file: 134038-87-2.mol

Synonyms:benzyl 5,17-bisbenzyloxy-14(S)-benzyloxycarbonylamino-11(S)-(3-benzyloxycarbonylamino-2(R)-hydroxypropyl)-10,13-dioxo-9,12-diazatricyclo[14.3.1.12,6]-henicosa-1(19),2,4,6(21),16(20),17-hexaene-8(S)-carboxylate

Chemical Property of benzyl 5,17-bisbenzyloxy-14(S)-benzyloxycarbonylamino-11(S)-(3-benzyloxycarbonylamino-2(R)-hydroxypropyl)-10,13-dioxo-9,12-diazatricyclo[14.3.1.12,6]-henicosa-1(19),2,4,6(21),16(20),17-hexaene-8(S)-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 5,17-bisbenzyloxy-14(S)-benzyloxycarbonylamino-11(S)-(3-benzyloxycarbonylamino-2(R)-hydroxypropyl)-10,13-dioxo-9,12-diazatricyclo[14.3.1.12,6]-henicosa-1(19),2,4,6(21),16(20),17-hexaene-8(S)-carboxylate

There total 38 articles about benzyl 5,17-bisbenzyloxy-14(S)-benzyloxycarbonylamino-11(S)-(3-benzyloxycarbonylamino-2(R)-hydroxypropyl)-10,13-dioxo-9,12-diazatricyclo[14.3.1.12,6]-henicosa-1(19),2,4,6(21),16(20),17-hexaene-8(S)-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: 85.0%

benzyl 2(S)-(5-benzyloxycarbonylamino-2(S)-tert-butoxycarbonylamino-4(R)-hydroxypentanoylamino)-3-[4,4'-bisbenzyloxy-3'-(2(S)-benzyloxycarbonylamino-2-pentafluorophenyloxycarbonylethyl)biphenyl-3-yl]propionate (134038-86-1) → benzyl 5,17-bisbenzyloxy-14(S)-benzyloxycarbonylamino-11(S)-(3-benzyloxycarbonylamino-2(R)-hydroxypropyl)-10,13-dioxo-9,12-diazatricyclo[14.3.1.12,6]-henicosa-1(19),2,4,6(21),16(20),17-hexaene-8(S)-carboxylate (134038-87-2)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 0 ℃; for 0.5h;

DOI:10.1055/s-1992-26293

Reference yield:

2-benzyloxy-5-bromobenzaldehyde (121124-94-5) → benzyl 5,17-bisbenzyloxy-14(S)-benzyloxycarbonylamino-11(S)-(3-benzyloxycarbonylamino-2(R)-hydroxypropyl)-10,13-dioxo-9,12-diazatricyclo[14.3.1.12,6]-henicosa-1(19),2,4,6(21),16(20),17-hexaene-8(S)-carboxylate (134038-87-2)

Guidance literature:

Multi-step reaction with 16 steps

1: 81 percent / BF₃*Et₂O / toluene / 3 h / Heating

3: 74 percent / N-bromosuccinimide, 2,6-lutidine / acetonitrile; CH₂Cl₂; H₂O / 0.17 h / 0 °C

4: 100 percent / tetramethylguanidine / tetrahydrofuran / 1) -70 deg C to r.t., overnight, 2) r.t., 1 d

5: 100 percent / LiOH / dioxane; H₂O / Ambient temperature

6: 100 percent / H₂ / (R,R)-*BF₄ / methanol / 72 h / 2250.2 Torr / Ambient temperature

7: 1) dicyclohexylcarbodiimide, 4-dimethylaminopyridine / 1) CH₂Cl₂, 0 deg C, 10 min, 2) 0 deg C, 1 h

8: 84 percent / pyridinium p-toluenesulfonate / acetone; H₂O / 6 h / Heating

9: 100 percent / tetramethylguanidine / tetrahydrofuran / 1) -70 deg C to r.t., overnight, 2) r.t., 1 d

10: 100 percent / H₂ / (R,R)-*BF₄ / methanol / 72 h / 2250.2 Torr / Ambient temperature

11: HCl / dioxane / 1 h / 0 °C

12: N-hydroxybenzotriazole, N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide*HCl / CH₂Cl₂ / -15 deg C to r.t., overnight

13: 83 percent / 90percent aq. AcOH / 2 h / 50 °C

14: 95 percent / Bu₄NF / dimethylformamide / 0.5 h / Ambient temperature

15: 98 percent / N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide*HCl / CH₂Cl₂ / -10 deg C to r.t., 12 h

16: 85 percent / HCl / dioxane / 0.5 h / 0 °C

With 2,6-dimethylpyridine; hydrogenchloride; dmap; lithium hydroxide; N-Bromosuccinimide; 1,1,3,3-tetramethylguanidine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; (R,R)-⁺BF4^-; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1055/s-1992-26293

Reference yield:

2-benzyloxy-5-iodobenzaldehyde (134038-89-4) → benzyl 5,17-bisbenzyloxy-14(S)-benzyloxycarbonylamino-11(S)-(3-benzyloxycarbonylamino-2(R)-hydroxypropyl)-10,13-dioxo-9,12-diazatricyclo[14.3.1.12,6]-henicosa-1(19),2,4,6(21),16(20),17-hexaene-8(S)-carboxylate (134038-87-2)

Guidance literature:

Multi-step reaction with 16 steps

1: 92 percent / BF₃*Et₂O / CHCl₃ / 24 h / Ambient temperature

3: 74 percent / N-bromosuccinimide, 2,6-lutidine / acetonitrile; CH₂Cl₂; H₂O / 0.17 h / 0 °C

4: 100 percent / tetramethylguanidine / tetrahydrofuran / 1) -70 deg C to r.t., overnight, 2) r.t., 1 d

5: 100 percent / LiOH / dioxane; H₂O / Ambient temperature

6: 100 percent / H₂ / (R,R)-*BF₄ / methanol / 72 h / 2250.2 Torr / Ambient temperature

7: 1) dicyclohexylcarbodiimide, 4-dimethylaminopyridine / 1) CH₂Cl₂, 0 deg C, 10 min, 2) 0 deg C, 1 h

8: 84 percent / pyridinium p-toluenesulfonate / acetone; H₂O / 6 h / Heating

9: 100 percent / tetramethylguanidine / tetrahydrofuran / 1) -70 deg C to r.t., overnight, 2) r.t., 1 d

10: 100 percent / H₂ / (R,R)-*BF₄ / methanol / 72 h / 2250.2 Torr / Ambient temperature

11: HCl / dioxane / 1 h / 0 °C

12: N-hydroxybenzotriazole, N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide*HCl / CH₂Cl₂ / -15 deg C to r.t., overnight

13: 83 percent / 90percent aq. AcOH / 2 h / 50 °C

14: 95 percent / Bu₄NF / dimethylformamide / 0.5 h / Ambient temperature

15: 98 percent / N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide*HCl / CH₂Cl₂ / -10 deg C to r.t., 12 h

16: 85 percent / HCl / dioxane / 0.5 h / 0 °C

With 2,6-dimethylpyridine; hydrogenchloride; dmap; lithium hydroxide; N-Bromosuccinimide; 1,1,3,3-tetramethylguanidine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; (R,R)-⁺BF4^-; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1055/s-1992-26293

upstream raw materials:

benzyl 2(S)-(5-benzyloxycarbonylamino-2(S)-tert-butoxycarbonylamino-4(R)-hydroxypentanoylamino)-3-[4,4'-bisbenzyloxy-3'-(2(S)-benzyloxycarbonylamino-2-pentafluorophenyloxycarbonylethyl)biphenyl-3-yl]propionate

5-iodosalicyclaldehyde

2-benzyloxy-5-bromobenzaldehyde

2-benzyloxy-5-iodobenzaldehyde

Downstream raw materials:

biphenomycin B

benzyl (8S,11S,14S)-5,17-bis(benzyloxy)-14-{[(benzyloxy)carbonyl]amino}-11-((2R)-3-{[(benzyloxy)carbonyl]amino}-2-{[tert-butyl(dimethyl)silyl]oxy}propyl)-10,13-dioxo-9,12-diazatricyclo[14.3.1.1{2,6}]henicosa-1⁽²⁰⁾,2⁽²¹⁾,3,5,16,18-hexaene-8-carboxylate

(8S,11S,14S)-5,17-bis(benzyloxy)-14-{[(benzyloxy)carbonyl]amino}-11-((2R)-3-{[(benzyloxy)carbonyl]amino}-2-{[tert-butyl(dimethyl)silyl]oxy}propyl)-10,13-dioxo-9,12-diazatricyclo[14.3.1.1{2,6}]henicosa-1⁽²⁰⁾,2⁽²¹⁾,3,5,16,18-hexaene-8-carboxylic acid