1,1'-[[(pentane-1,5-diyl)dioxy]-bis[(2-amino-5-methoxy-1,4-phenylene)carbonyl]]-bis[(2S,4R)-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine]

Base Information

• Chemical Name: 1,1'-[[(pentane-1,5-diyl)dioxy]-bis[(2-amino-5-methoxy-1,4-phenylene)carbonyl]]-bis[(2S,4R)-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine]
• CAS No.: 260418-26-6
• Molecular Formula: C₄₃H₇₂N₄O₁₀Si₂
• Molecular Weight: 861.236
• Mol file: 260418-26-6.mol

Synonyms:1,1'-[[(pentane-1,5-diyl)dioxy]-bis[(2-amino-5-methoxy-1,4-phenylene)carbonyl]]-bis[(2S,4R)-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine]

Chemical Property of 1,1'-[[(pentane-1,5-diyl)dioxy]-bis[(2-amino-5-methoxy-1,4-phenylene)carbonyl]]-bis[(2S,4R)-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,1'-[[(pentane-1,5-diyl)dioxy]-bis[(2-amino-5-methoxy-1,4-phenylene)carbonyl]]-bis[(2S,4R)-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine]

There total 13 articles about 1,1'-[[(pentane-1,5-diyl)dioxy]-bis[(2-amino-5-methoxy-1,4-phenylene)carbonyl]]-bis[(2S,4R)-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine] 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: 91.0%

(S,R)-((pentane-1,5-diylbis(oxy))bis(5-methoxy-2-nitro-4,1-phenylene))bis(((2S,4R)-2-(((tert-butyldimethylsllyl)oxy)methyl)-4-hydroxypyrrolidin-1-yl) methanone) (260418-25-5) → 1,1'-[[(pentane-1,5-diyl)dioxy]-bis[(2-amino-5-methoxy-1,4-phenylene)carbonyl]]-bis[(2S,4R)-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine] (260418-26-6)

Guidance literature:

With hydrazine hydrate; nickel; In methanol; for 1h; Heating;

DOI:10.1021/jm030897l

Reference yield:

4-hydroxy-3-methoxybenzoic acid methyl ester (3943-74-6) → 1,1'-[[(pentane-1,5-diyl)dioxy]-bis[(2-amino-5-methoxy-1,4-phenylene)carbonyl]]-bis[(2S,4R)-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine] (260418-26-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: diethyl azodicarboxylate; Ph₃P / tetrahydrofuran / 1 h / 0 °C

1.2: tetrahydrofuran / 20 °C

2.1: Cu(NO₃)2*3H₂O; acetic anhydride / 0 - 20 °C

3.1: 100 percent / aq. NaOH / tetrahydrofuran / 72 h

4.1: oxalyl chloride; DMF / tetrahydrofuran

5.1: 5.29 g / Et₃N / tetrahydrofuran; H₂O / 3 h / 20 °C

6.1: 91 percent / hydrazine hydrate / Raney nickel / methanol / 1 h / Heating

With sodium hydroxide; oxalyl dichloride; acetic anhydride; copper(II) nitrate; hydrazine hydrate; triethylamine; N,N-dimethyl-formamide; triphenylphosphine; diethylazodicarboxylate; nickel; In tetrahydrofuran; methanol; water; 1.1: Mitsunobu etherification;

DOI:10.1021/jm030897l

Reference yield:

1 ,5-pentanediol (111-29-5) → 1,1'-[[(pentane-1,5-diyl)dioxy]-bis[(2-amino-5-methoxy-1,4-phenylene)carbonyl]]-bis[(2S,4R)-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine] (260418-26-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: diethyl azodicarboxylate; Ph₃P / tetrahydrofuran / 1 h / 0 °C

1.2: tetrahydrofuran / 20 °C

2.1: Cu(NO₃)2*3H₂O; acetic anhydride / 0 - 20 °C

3.1: 100 percent / aq. NaOH / tetrahydrofuran / 72 h

4.1: oxalyl chloride; DMF / tetrahydrofuran

5.1: 5.29 g / Et₃N / tetrahydrofuran; H₂O / 3 h / 20 °C

6.1: 91 percent / hydrazine hydrate / Raney nickel / methanol / 1 h / Heating

With sodium hydroxide; oxalyl dichloride; acetic anhydride; copper(II) nitrate; hydrazine hydrate; triethylamine; N,N-dimethyl-formamide; triphenylphosphine; diethylazodicarboxylate; nickel; In tetrahydrofuran; methanol; water; 1.1: Mitsunobu etherification;

DOI:10.1021/jm030897l

upstream raw materials:

(S,R)-((pentane-1,5-diylbis(oxy))bis(5-methoxy-2-nitro-4,1-phenylene))bis(((2S,4R)-2-(((tert-butyldimethylsllyl)oxy)methyl)-4-hydroxypyrrolidin-1-yl) methanone)

4-hydroxy-3-methoxybenzoic acid methyl ester

1 ,5-pentanediol

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate

Downstream raw materials:

1,1'-[[(pentane-1,5-diyl)dioxy]-bis[(2-amino-N-allyloxycarbonyl-5-methoxy-1,4-phenylene)carbonyl]]-bis[(2S,4R)-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine]

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

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

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