[4-[3-[4-[(2S)-2-(hydroxymethyl)-4-methylene-pyrrolidine-1-carbonyl]-2-methoxy-5-nitrophenoxy]propoxy]-5-methoxy-2-nitro-phenyl]-[(2S)-2-(hydroxymethyl)-4-methylene-pyrrolidin-1-yl]methanone

Base Information

• Chemical Name: [4-[3-[4-[(2S)-2-(hydroxymethyl)-4-methylene-pyrrolidine-1-carbonyl]-2-methoxy-5-nitrophenoxy]propoxy]-5-methoxy-2-nitro-phenyl]-[(2S)-2-(hydroxymethyl)-4-methylene-pyrrolidin-1-yl]methanone
• CAS No.: 232931-61-2
• Molecular Formula: C₃₁H₃₆N₄O₁₂
• Molecular Weight: 656.646

Synonyms:[4-[3-[4-[(2S)-2-(hydroxymethyl)-4-methylene-pyrrolidine-1-carbonyl]-2-methoxy-5-nitrophenoxy]propoxy]-5-methoxy-2-nitro-phenyl]-[(2S)-2-(hydroxymethyl)-4-methylene-pyrrolidin-1-yl]methanone

Chemical Property of [4-[3-[4-[(2S)-2-(hydroxymethyl)-4-methylene-pyrrolidine-1-carbonyl]-2-methoxy-5-nitrophenoxy]propoxy]-5-methoxy-2-nitro-phenyl]-[(2S)-2-(hydroxymethyl)-4-methylene-pyrrolidin-1-yl]methanone

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Technology Process of [4-[3-[4-[(2S)-2-(hydroxymethyl)-4-methylene-pyrrolidine-1-carbonyl]-2-methoxy-5-nitrophenoxy]propoxy]-5-methoxy-2-nitro-phenyl]-[(2S)-2-(hydroxymethyl)-4-methylene-pyrrolidin-1-yl]methanone

There total 15 articles about [4-[3-[4-[(2S)-2-(hydroxymethyl)-4-methylene-pyrrolidine-1-carbonyl]-2-methoxy-5-nitrophenoxy]propoxy]-5-methoxy-2-nitro-phenyl]-[(2S)-2-(hydroxymethyl)-4-methylene-pyrrolidin-1-yl]methanone 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: 94.0%

[4-[3-[4-[(2S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-methylenepyrrolidine-1-carbonyl]-2-methoxy-5-nitrophenoxy]propoxy]-5-methoxy-2-nitrophenyl]-[(2S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-methylene-pyrrolidin-1-yl]methanone (232931-60-1) → [4-[3-[4-[(2S)-2-(hydroxymethyl)-4-methylene-pyrrolidine-1-carbonyl]-2-methoxy-5-nitrophenoxy]propoxy]-5-methoxy-2-nitro-phenyl]-[(2S)-2-(hydroxymethyl)-4-methylene-pyrrolidin-1-yl]methanone (232931-61-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 0.5h;

DOI:10.1021/jm001064n

Reference yield: 72.0%

dimethyl 1,1‘-(4,4‘-(propane-1,3-diylbis(oxy))bis(5-methoxy-2-nitrobenzoyl))(2S,2'S)-bis(4-methylenepyrrolidine-2-carboxylate) → [4-[3-[4-[(2S)-2-(hydroxymethyl)-4-methylene-pyrrolidine-1-carbonyl]-2-methoxy-5-nitrophenoxy]propoxy]-5-methoxy-2-nitro-phenyl]-[(2S)-2-(hydroxymethyl)-4-methylene-pyrrolidin-1-yl]methanone (232931-61-2)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; at 0 - 20 ℃; for 2.5h; Inert atmosphere;

Reference yield:

1',3'-bis(4-carboxy-2-methoxy-5-nitrophenoxy)propane (140658-45-3) → [4-[3-[4-[(2S)-2-(hydroxymethyl)-4-methylene-pyrrolidine-1-carbonyl]-2-methoxy-5-nitrophenoxy]propoxy]-5-methoxy-2-nitro-phenyl]-[(2S)-2-(hydroxymethyl)-4-methylene-pyrrolidin-1-yl]methanone (232931-61-2)

Guidance literature:

Multi-step reaction with 3 steps

1: oxalyl chloride; DMF / tetrahydrofuran / 16 h

2: Et₃N / tetrahydrofuran; H₂O / 2 h / 20 °C

3: 94 percent / TBAF / tetrahydrofuran / 0.5 h / 0 - 20 °C

With oxalyl dichloride; tetrabutyl ammonium fluoride; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; water;

DOI:10.1021/jm001064n

upstream raw materials:

[4-[3-[4-[(2S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-methylenepyrrolidine-1-carbonyl]-2-methoxy-5-nitrophenoxy]propoxy]-5-methoxy-2-nitrophenyl]-[(2S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-methylene-pyrrolidin-1-yl]methanone

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

(2S,4R)-N-(allyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

4R-4-hydroxyproline

Downstream raw materials:

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

1,1'-[[(propane-1,3-diyl)dioxy]bis[(11aS)-7-methoxy-2-methylidene-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one]]

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

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