1,1'-[[(propane-1,3-diyl)dioxy]bis[2-amino-N-allyloxycarbonyl-5-methoxy-1,4-phenylene]-carbonyl]-bis[(2S)-2-t-butyldimethylsilyloxymethyl-4-methoxycarbonyl methyl-2,3-dihydropyrrole]

Base Information

• Chemical Name: 1,1'-[[(propane-1,3-diyl)dioxy]bis[2-amino-N-allyloxycarbonyl-5-methoxy-1,4-phenylene]-carbonyl]-bis[(2S)-2-t-butyldimethylsilyloxymethyl-4-methoxycarbonyl methyl-2,3-dihydropyrrole]
• CAS No.: 260417-99-0
• Molecular Formula: C₅₅H₈₀N₄O₁₆Si₂
• Molecular Weight: 1109.43
• Mol file: 260417-99-0.mol

Synonyms:1,1'-[[(propane-1,3-diyl)dioxy]bis[2-amino-N-allyloxycarbonyl-5-methoxy-1,4-phenylene]-carbonyl]-bis[(2S)-2-t-butyldimethylsilyloxymethyl-4-methoxycarbonyl methyl-2,3-dihydropyrrole]

Chemical Property of 1,1'-[[(propane-1,3-diyl)dioxy]bis[2-amino-N-allyloxycarbonyl-5-methoxy-1,4-phenylene]-carbonyl]-bis[(2S)-2-t-butyldimethylsilyloxymethyl-4-methoxycarbonyl methyl-2,3-dihydropyrrole]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,1'-[[(propane-1,3-diyl)dioxy]bis[2-amino-N-allyloxycarbonyl-5-methoxy-1,4-phenylene]-carbonyl]-bis[(2S)-2-t-butyldimethylsilyloxymethyl-4-methoxycarbonyl methyl-2,3-dihydropyrrole]

There total 7 articles about 1,1'-[[(propane-1,3-diyl)dioxy]bis[2-amino-N-allyloxycarbonyl-5-methoxy-1,4-phenylene]-carbonyl]-bis[(2S)-2-t-butyldimethylsilyloxymethyl-4-methoxycarbonyl methyl-2,3-dihydropyrrole] 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: 88.0%

Methyl diethylphosphonoacetate (1067-74-9) + 1,1'-[[(propane-1,3-diyl)dioxy]-bis[(2-amino-N-allyloxycarbonyl-5-methoxy-1,4-phenylene)carbonyl]]-bis[(2S)-2-t-butyldimethylsilyloxymethyl-4-oxo-pyrrolidine] (260417-98-9) → 1,1'-[[(propane-1,3-diyl)dioxy]bis[2-amino-N-allyloxycarbonyl-5-methoxy-1,4-phenylene]-carbonyl]-bis[(2S)-2-t-butyldimethylsilyloxymethyl-4-methoxycarbonyl methyl-2,3-dihydropyrrole] (260417-99-0)

Guidance literature:

Methyl diethylphosphonoacetate; With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

1,1'-[[(propane-1,3-diyl)dioxy]-bis[(2-amino-N-allyloxycarbonyl-5-methoxy-1,4-phenylene)carbonyl]]-bis[(2S)-2-t-butyldimethylsilyloxymethyl-4-oxo-pyrrolidine]; In tetrahydrofuran; at 0 - 20 ℃; for 18h;

Reference yield:

1',3'-bis(4-carboxy-2-methoxyphenoxy)propane (3018-48-2) → 1,1'-[[(propane-1,3-diyl)dioxy]bis[2-amino-N-allyloxycarbonyl-5-methoxy-1,4-phenylene]-carbonyl]-bis[(2S)-2-t-butyldimethylsilyloxymethyl-4-methoxycarbonyl methyl-2,3-dihydropyrrole] (260417-99-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 70 percent / 70 percent aq. HNO₃ / 12 h / 10 °C

2: (COCl)2; DMF / tetrahydrofuran / 16 h

3: TEA / H₂O / 16 h / 0 °C

4: 93 percent / NH₂NH₂; Raney Ni / methanol / 1 h / Heating

5: 84 percent / pyridine / CH₂Cl₂ / 2.5 h / 0 °C

6: 59 percent / (COCl)2; DMSO; TEA / CH₂Cl₂ / -60 °C

7: 79 percent / NaH / tetrahydrofuran / 16 h / 0 °C

With pyridine; oxalyl dichloride; TEA; nitric acid; nickel; sodium hydride; dimethyl sulfoxide; N,N-dimethyl-formamide; hydrazine; In tetrahydrofuran; methanol; dichloromethane; water; 6: Swern oxidation / 7: Horner-Emmons reaction;

DOI:10.1016/S0960-894X(01)00560-1

Reference yield:

1',3'-bis(4-carboxy-2-methoxy-5-nitrophenoxy)propane (140658-45-3) → 1,1'-[[(propane-1,3-diyl)dioxy]bis[2-amino-N-allyloxycarbonyl-5-methoxy-1,4-phenylene]-carbonyl]-bis[(2S)-2-t-butyldimethylsilyloxymethyl-4-methoxycarbonyl methyl-2,3-dihydropyrrole] (260417-99-0)

Guidance literature:

Multi-step reaction with 6 steps

1: (COCl)2; DMF / tetrahydrofuran / 16 h

2: TEA / H₂O / 16 h / 0 °C

3: 93 percent / NH₂NH₂; Raney Ni / methanol / 1 h / Heating

4: 84 percent / pyridine / CH₂Cl₂ / 2.5 h / 0 °C

5: 59 percent / (COCl)2; DMSO; TEA / CH₂Cl₂ / -60 °C

6: 79 percent / NaH / tetrahydrofuran / 16 h / 0 °C

With pyridine; oxalyl dichloride; TEA; nickel; sodium hydride; dimethyl sulfoxide; N,N-dimethyl-formamide; hydrazine; In tetrahydrofuran; methanol; dichloromethane; water; 5: Swern oxidation / 6: Horner-Emmons reaction;

DOI:10.1016/S0960-894X(01)00560-1

upstream raw materials:

Methyl diethylphosphonoacetate

1,1'-[[(propane-1,3-diyl)dioxy]-bis[(2-amino-N-allyloxycarbonyl-5-methoxy-1,4-phenylene)carbonyl]]-bis[(2S)-2-t-butyldimethylsilyloxymethyl-4-oxo-pyrrolidine]

1',3'-bis(4-carboxy-2-methoxyphenoxy)propane

1',3'-bis(4-carboxy-2-methoxy-5-nitrophenoxy)propane

Downstream raw materials:

1,1'-[[(propane-1,3-diyl)dioxy]bis[2-amino-N-allyloxycarbonyl-5-methoxy-1,4-phenylene]-carbonyl]-bis[(2S)-2-hydroxymethyl-4-methoxycarbonylmethyl-2,3-dihydropyrrole]

Refernces

• 1、 -. "Pyrrolobenzodiazepines". Page 38, 105. . Retrieved 2010/11/29.