2-{1-[1-tert-Butoxycarbonyl-5-((Z)-8-trityloxy-oct-1-enyl)-1H-pyrrol-3-yl]-2-methyl-propyl}-malonic acid dimethyl ester

Base Information

• Chemical Name: 2-{1-[1-tert-Butoxycarbonyl-5-((Z)-8-trityloxy-oct-1-enyl)-1H-pyrrol-3-yl]-2-methyl-propyl}-malonic acid dimethyl ester
• CAS No.: 244035-24-3
• Molecular Formula: C₄₅H₅₅NO₇
• Molecular Weight: 721.934
• Mol file: 244035-24-3.mol

Synonyms:2-{1-[1-tert-Butoxycarbonyl-5-((Z)-8-trityloxy-oct-1-enyl)-1H-pyrrol-3-yl]-2-methyl-propyl}-malonic acid dimethyl ester

Chemical Property of 2-{1-[1-tert-Butoxycarbonyl-5-((Z)-8-trityloxy-oct-1-enyl)-1H-pyrrol-3-yl]-2-methyl-propyl}-malonic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{1-[1-tert-Butoxycarbonyl-5-((Z)-8-trityloxy-oct-1-enyl)-1H-pyrrol-3-yl]-2-methyl-propyl}-malonic acid dimethyl ester

There total 7 articles about 2-{1-[1-tert-Butoxycarbonyl-5-((Z)-8-trityloxy-oct-1-enyl)-1H-pyrrol-3-yl]-2-methyl-propyl}-malonic acid dimethyl ester 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%

2-[1-(1-tert-Butoxycarbonyl-5-formyl-1H-pyrrol-3-yl)-2-methyl-propyl]-malonic acid dimethyl ester (214337-84-5) + Triphenyl-(7-trityloxy-heptyl)-phosphonium; bromide → 2-{1-[1-tert-Butoxycarbonyl-5-((Z)-8-trityloxy-oct-1-enyl)-1H-pyrrol-3-yl]-2-methyl-propyl}-malonic acid dimethyl ester (244035-24-3)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/S0040-4039(98)01450-6

Reference yield:

pyrrole-3-carboxaldehyde (7126-39-8) → 2-{1-[1-tert-Butoxycarbonyl-5-((Z)-8-trityloxy-oct-1-enyl)-1H-pyrrol-3-yl]-2-methyl-propyl}-malonic acid dimethyl ester (244035-24-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / piperidine / pyridine / 70 °C

2: 81 percent / tetrahydrofuran / -78 °C

3: 96 percent / POCl₃; AcONa / 0 deg C to room temp.; H₂O, 60 deg C

4: 80 percent / DMAP / acetonitrile / Ambient temperature

5: 88 percent / NaHMDS / tetrahydrofuran / -78 - 20 °C

With piperidine; dmap; sodium acetate; sodium hexamethyldisilazane; trichlorophosphate; In tetrahydrofuran; pyridine; acetonitrile;

DOI:10.1016/S0040-4039(98)01450-6

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 2-{1-[1-tert-Butoxycarbonyl-5-((Z)-8-trityloxy-oct-1-enyl)-1H-pyrrol-3-yl]-2-methyl-propyl}-malonic acid dimethyl ester (244035-24-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / DMAP / acetonitrile / Ambient temperature

2: 88 percent / NaHMDS / tetrahydrofuran / -78 - 20 °C

With dmap; sodium hexamethyldisilazane; In tetrahydrofuran; acetonitrile;

DOI:10.1016/S0040-4039(98)01450-6

upstream raw materials:

2-[1-(1-tert-Butoxycarbonyl-5-formyl-1H-pyrrol-3-yl)-2-methyl-propyl]-malonic acid dimethyl ester

pyrrole-3-carboxaldehyde

di-tert-butyl dicarbonate

malonic acid dimethyl ester