(S)-4-<5-Benzyloxycarbonyl-3-(2-methoxycarbonylethyl)-4-(methoxycarbonylmethyl)pyrrol-2-ylmethyl>-2,8-bis(2-methoxycarbonylethyl)-3,7-bis(methoxycarbonylmethyl)-9-(2,2,2-tribromoethoxycarbonyl)-4,5-dihydrodipyrrin-1(10H)-one

Base Information

• Chemical Name: (S)-4-<5-Benzyloxycarbonyl-3-(2-methoxycarbonylethyl)-4-(methoxycarbonylmethyl)pyrrol-2-ylmethyl>-2,8-bis(2-methoxycarbonylethyl)-3,7-bis(methoxycarbonylmethyl)-9-(2,2,2-tribromoethoxycarbonyl)-4,5-dihydrodipyrrin-1(10H)-one
• CAS No.: 135100-99-1
• Molecular Formula: C₄₆H₅₂Br₃N₃O₁₇
• Molecular Weight: 1158.64

Synonyms:(S)-4-<5-Benzyloxycarbonyl-3-(2-methoxycarbonylethyl)-4-(methoxycarbonylmethyl)pyrrol-2-ylmethyl>-2,8-bis(2-methoxycarbonylethyl)-3,7-bis(methoxycarbonylmethyl)-9-(2,2,2-tribromoethoxycarbonyl)-4,5-dihydrodipyrrin-1(10H)-one

Chemical Property of (S)-4-<5-Benzyloxycarbonyl-3-(2-methoxycarbonylethyl)-4-(methoxycarbonylmethyl)pyrrol-2-ylmethyl>-2,8-bis(2-methoxycarbonylethyl)-3,7-bis(methoxycarbonylmethyl)-9-(2,2,2-tribromoethoxycarbonyl)-4,5-dihydrodipyrrin-1(10H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (S)-4-<5-Benzyloxycarbonyl-3-(2-methoxycarbonylethyl)-4-(methoxycarbonylmethyl)pyrrol-2-ylmethyl>-2,8-bis(2-methoxycarbonylethyl)-3,7-bis(methoxycarbonylmethyl)-9-(2,2,2-tribromoethoxycarbonyl)-4,5-dihydrodipyrrin-1(10H)-one

There total 24 articles about (S)-4-<5-Benzyloxycarbonyl-3-(2-methoxycarbonylethyl)-4-(methoxycarbonylmethyl)pyrrol-2-ylmethyl>-2,8-bis(2-methoxycarbonylethyl)-3,7-bis(methoxycarbonylmethyl)-9-(2,2,2-tribromoethoxycarbonyl)-4,5-dihydrodipyrrin-1(10H)-one 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: 97.0%

methanol (67-56-1) + (S)-3-[(3R,4R,5R)-4,5-((R)-Benzylidenedioxy)-2-oxotetrahydropyran-3-yloxycarbonylmethyl]-4-[5-benzyloxycarbonyl-3-(2-methoxycarbonylethyl)-4-methoxycarbonylmethylpyrrol-2-ylmethyl]-2,8-bis(2-methoxycarbonylethyl)-7-methoxycarbonylmethyl-9-(2,2,2-... (135129-41-8) → (S)-4-<5-Benzyloxycarbonyl-3-(2-methoxycarbonylethyl)-4-(methoxycarbonylmethyl)pyrrol-2-ylmethyl>-2,8-bis(2-methoxycarbonylethyl)-3,7-bis(methoxycarbonylmethyl)-9-(2,2,2-tribromoethoxycarbonyl)-4,5-dihydrodipyrrin-1(10H)-one (135100-99-1)

Guidance literature:

With sodium methylate; In tetrahydrofuran; for 0.416667h; Ambient temperature;

DOI:10.1039/p19960002079

Reference yield:

4-acetyl-3-(2-methoxycarbonyl-ethyl)-5-methyl-pyrrole-2-carboxylic acid benzyl ester (62916-29-4) → (S)-4-<5-Benzyloxycarbonyl-3-(2-methoxycarbonylethyl)-4-(methoxycarbonylmethyl)pyrrol-2-ylmethyl>-2,8-bis(2-methoxycarbonylethyl)-3,7-bis(methoxycarbonylmethyl)-9-(2,2,2-tribromoethoxycarbonyl)-4,5-dihydrodipyrrin-1(10H)-one (135100-99-1)

Guidance literature:

Multi-step reaction with 13 steps

1: 7 percent / Tl(NO₃)3*3H₂O, conc. HNO₃ / 1,2-dimethoxy-ethane / 28 h / Ambient temperature

2: SO₂Cl₂ / CH₂Cl₂ / 1 h / 0 °C

3: NaOAc / 1.5 h / 60 °C

4: 98 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 1.5 h / Ambient temperature

5: 96 percent / DCC / CH₂Cl₂ / 1.5 h

6: 84 percent / p-TsOH / CH₂Cl₂ / 2 h / Ambient temperature

7: 63 percent / SnCl₄ / CH₂Cl₂ / 0.67 h / -10 - 5 °C

8: aq. NaHCO₃, KI₃ / CH₂Cl₂ / 0.58 h

9: 1.) SnCl₄, 2.) aq. p-TsOH, AgOAc / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) THF, 17 h

10: 71 percent / TBAF*3H₂O / tetrahydrofuran / 1 h / Ambient temperature

11: 1-chloro-1-dimethylamino-2-methylprop-1-ene / CH₂Cl₂ / 0.33 h / Ambient temperature

12: CH₂Cl₂ / 3 h / Ambient temperature

13: 97 percent / NaOMe / tetrahydrofuran / 0.42 h / Ambient temperature

With sulfuryl dichloride; potassium triiodide; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; tetrabutyl ammonium fluoride; hydrogen; nitric acid; sodium methylate; silver(I) acetate; sodium acetate; tin(IV) chloride; sodium hydrogencarbonate; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; thallium(III) nitrate; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane;

DOI:10.1039/p19960002079

Reference yield:

3-(2-methoxycarbonyl-ethyl)-5-methyl-pyrrole-2,4-dicarboxylic acid 2-benzyl ester (53365-81-4) → (S)-4-<5-Benzyloxycarbonyl-3-(2-methoxycarbonylethyl)-4-(methoxycarbonylmethyl)pyrrol-2-ylmethyl>-2,8-bis(2-methoxycarbonylethyl)-3,7-bis(methoxycarbonylmethyl)-9-(2,2,2-tribromoethoxycarbonyl)-4,5-dihydrodipyrrin-1(10H)-one (135100-99-1)

Guidance literature:

Multi-step reaction with 16 steps

1: aq. NaHCO₃, KI₃ / 1,2-dichloro-ethane / 0.5 h / Heating

2: 1.) 57percent aq. HI, Ac₂O, 50percent aq. H₃PO₂ / 1.) 0 deg C, 5 min, 2.) 0 deg C, 20 min

3: (COCl)2, DMF / CH₂Cl₂ / 0.5 h / Ambient temperature

4: DMAP / CH₂Cl₂ / 0.33 h / Ambient temperature

5: SO₂Cl₂ / CH₂Cl₂ / 1 h / 0 °C

6: NaOAc / 1.5 h / 60 °C

7: 98 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 1.5 h / Ambient temperature

8: 96 percent / DCC / CH₂Cl₂ / 1.5 h

9: 84 percent / p-TsOH / CH₂Cl₂ / 2 h / Ambient temperature

10: 63 percent / SnCl₄ / CH₂Cl₂ / 0.67 h / -10 - 5 °C

11: aq. NaHCO₃, KI₃ / CH₂Cl₂ / 0.58 h

12: 1.) SnCl₄, 2.) aq. p-TsOH, AgOAc / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) THF, 17 h

13: 71 percent / TBAF*3H₂O / tetrahydrofuran / 1 h / Ambient temperature

14: 1-chloro-1-dimethylamino-2-methylprop-1-ene / CH₂Cl₂ / 0.33 h / Ambient temperature

15: CH₂Cl₂ / 3 h / Ambient temperature

16: 97 percent / NaOMe / tetrahydrofuran / 0.42 h / Ambient temperature

With dmap; sulfuryl dichloride; oxalyl dichloride; potassium triiodide; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; tetrabutyl ammonium fluoride; hydrogen iodide; hydrogen; sodium methylate; silver(I) acetate; sodium acetate; hypophosphorous acid; acetic anhydride; tin(IV) chloride; sodium hydrogencarbonate; toluene-4-sulfonic acid; N,N-dimethyl-formamide; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1039/p19960002079

upstream raw materials:

methanol

(S)-3-[(3R,4R,5R)-4,5-((R)-Benzylidenedioxy)-2-oxotetrahydropyran-3-yloxycarbonylmethyl]-4-[5-benzyloxycarbonyl-3-(2-methoxycarbonylethyl)-4-methoxycarbonylmethylpyrrol-2-ylmethyl]-2,8-bis(2-methoxycarbonylethyl)-7-methoxycarbonylmethyl-9-(2,2,2-...

4-acetyl-3-(2-methoxycarbonyl-ethyl)-5-methyl-pyrrole-2-carboxylic acid benzyl ester

3-(2-methoxycarbonyl-ethyl)-5-methyl-pyrrole-2,4-dicarboxylic acid 2-benzyl ester

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