(4S,7S,10S,2’R)-10-benzyoxycarbonylamino-1¹,2¹-bis-methoxy-7-[3’-azido-2’-(tert-butyldimethyl-silyloxy)propyl]-5,8-diaza-6,9-dioxo-1,2(4,2)-dibenzenacycloundecaphane-4-methyl carboxylate

Base Information

• Chemical Name: (4S,7S,10S,2’R)-10-benzyoxycarbonylamino-1¹,2¹-bis-methoxy-7-[3’-azido-2’-(tert-butyldimethyl-silyloxy)propyl]-5,8-diaza-6,9-dioxo-1,2(4,2)-dibenzenacycloundecaphane-4-methyl carboxylate
• CAS No.: 1095089-51-2
• Molecular Formula: C₄₀H₅₂N₆O₉Si
• Molecular Weight: 788.973
• Mol file: 1095089-51-2.mol

Synonyms:(4S,7S,10S,2’R)-10-benzyoxycarbonylamino-1¹,2¹-bis-methoxy-7-[3’-azido-2’-(tert-butyldimethyl-silyloxy)propyl]-5,8-diaza-6,9-dioxo-1,2(4,2)-dibenzenacycloundecaphane-4-methyl carboxylate

Chemical Property of (4S,7S,10S,2’R)-10-benzyoxycarbonylamino-1¹,2¹-bis-methoxy-7-[3’-azido-2’-(tert-butyldimethyl-silyloxy)propyl]-5,8-diaza-6,9-dioxo-1,2(4,2)-dibenzenacycloundecaphane-4-methyl carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,7S,10S,2’R)-10-benzyoxycarbonylamino-1¹,2¹-bis-methoxy-7-[3’-azido-2’-(tert-butyldimethyl-silyloxy)propyl]-5,8-diaza-6,9-dioxo-1,2(4,2)-dibenzenacycloundecaphane-4-methyl carboxylate

There total 16 articles about (4S,7S,10S,2’R)-10-benzyoxycarbonylamino-1¹,2¹-bis-methoxy-7-[3’-azido-2’-(tert-butyldimethyl-silyloxy)propyl]-5,8-diaza-6,9-dioxo-1,2(4,2)-dibenzenacycloundecaphane-4-methyl 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: 75.0%

C40H54N6O10Si (1095089-49-8) → (4S,7S,10S,2’R)-10-benzyoxycarbonylamino-11,21-bis-methoxy-7-[3’-azido-2’-(tert-butyldimethyl-silyloxy)propyl]-5,8-diaza-6,9-dioxo-1,2(4,2)-dibenzenacycloundecaphane-4-methyl carboxylate (1095089-51-2)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate(V); N-ethyl-N,N-diisopropylamine; In dichloromethane; for 30h; Inert atmosphere;

DOI:10.1039/b811583d

Reference yield:

(S)-2-amino-3-(5'-iodo-2'-methoxyphenyl)propanoic acid hydrochloride (1095089-33-0) → (4S,7S,10S,2’R)-10-benzyoxycarbonylamino-11,21-bis-methoxy-7-[3’-azido-2’-(tert-butyldimethyl-silyloxy)propyl]-5,8-diaza-6,9-dioxo-1,2(4,2)-dibenzenacycloundecaphane-4-methyl carboxylate (1095089-51-2)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydrogencarbonate / 1,4-dioxane; water / 16.17 h / 0 - 20 °C / Inert atmosphere

2: caesium carbonate; palladium diacetate; tris-(o-tolyl)phosphine / 1,4-dioxane; water / 8 h / 80 °C / Inert atmosphere

3: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

4: 2,6-dimethylpyridine; triethylsilyl trifluoromethyl sulfonate / dichloromethane / 16 h / 20 °C / Inert atmosphere

5: N-ethyl-N,N-diisopropylamine; HATU; 1-hydroxy-7-aza-benzotriazole / dichloromethane / 38 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole; triethylsilyl trifluoromethyl sulfonate; palladium diacetate; sodium hydrogencarbonate; benzotriazol-1-ol; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; HATU; tris-(o-tolyl)phosphine; In 1,4-dioxane; dichloromethane; water; 2: |Suzuki Coupling;

DOI:10.1002/asia.201000908

Reference yield:

(2S,4R)-N-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)pyrrolidine-2-carboxylic acid tert-butyl ester (1095089-41-0) → (4S,7S,10S,2’R)-10-benzyoxycarbonylamino-11,21-bis-methoxy-7-[3’-azido-2’-(tert-butyldimethyl-silyloxy)propyl]-5,8-diaza-6,9-dioxo-1,2(4,2)-dibenzenacycloundecaphane-4-methyl carboxylate (1095089-51-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: ruthenium(IV) oxide hydrate; sodium periodate / water; ethyl acetate / 20 h / 20 °C / Inert atmosphere

2.1: sodium tetrahydroborate / water; ethanol / 22 h / 0 - 20 °C / pH 7 / Inert atmosphere

3.1: triphenylphosphine; hydrogen azide; di-isopropyl azodicarboxylate / toluene / 4 h / Inert atmosphere

4.1: 2,6-dimethylpyridine; t-butyldimethylsiyl triflate / dichloromethane / 0.25 h / 20 °C / Inert atmosphere

4.2: 1 h / Inert atmosphere

5.1: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

6.1: 2,6-dimethylpyridine; triethylsilyl trifluoromethyl sulfonate / dichloromethane / 16 h / 20 °C / Inert atmosphere

7.1: N-ethyl-N,N-diisopropylamine; HATU; 1-hydroxy-7-aza-benzotriazole / dichloromethane / 38 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; hydrogen azide; 1-hydroxy-7-aza-benzotriazole; ruthenium(IV) oxide hydrate; di-isopropyl azodicarboxylate; t-butyldimethylsiyl triflate; triethylsilyl trifluoromethyl sulfonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; HATU; In ethanol; dichloromethane; water; ethyl acetate; toluene; 3.1: |Mitsunobu Displacement;

DOI:10.1002/asia.201000908

upstream raw materials:

C₄₀H₅₄N₆O₁₀Si

(2S,2’’’S)-2-(benzyloxcarbonylamino)-3-(4’,4’’-bis-methoxy-3’’-[tert-butyloxycarbonylamino-2’’’-methoxycarbonylethyl]-biphenyl-3’-yl)-propionic acid

(2S,4R)-N-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)pyrrolidine-2-carboxylic acid tert-butyl ester

(2S,4R)-N-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-5-oxopyrrolidine-2-carboxylic acid tert-butyl ester

Downstream raw materials:

C₃₉H₅₂N₄O₉Si

C₃₃H₃₈N₄O₉