4-[(8R,9S,13S,14S,16S,17S)-16-(3-Azido-propyl)-13-methyl-17-(tetrahydro-pyran-2-yloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yloxymethyl]-3-nitro-benzoic acid

Base Information

• Chemical Name: 4-[(8R,9S,13S,14S,16S,17S)-16-(3-Azido-propyl)-13-methyl-17-(tetrahydro-pyran-2-yloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yloxymethyl]-3-nitro-benzoic acid
• CAS No.: 220810-56-0
• Molecular Formula: C₃₄H₄₂N₄O₇
• Molecular Weight: 618.73
• Mol file: 220810-56-0.mol

Synonyms:4-[(8R,9S,13S,14S,16S,17S)-16-(3-Azido-propyl)-13-methyl-17-(tetrahydro-pyran-2-yloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yloxymethyl]-3-nitro-benzoic acid

Chemical Property of 4-[(8R,9S,13S,14S,16S,17S)-16-(3-Azido-propyl)-13-methyl-17-(tetrahydro-pyran-2-yloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yloxymethyl]-3-nitro-benzoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[(8R,9S,13S,14S,16S,17S)-16-(3-Azido-propyl)-13-methyl-17-(tetrahydro-pyran-2-yloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yloxymethyl]-3-nitro-benzoic acid

There total 9 articles about 4-[(8R,9S,13S,14S,16S,17S)-16-(3-Azido-propyl)-13-methyl-17-(tetrahydro-pyran-2-yloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yloxymethyl]-3-nitro-benzoic acid 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: 83.0%

4-[(8R,9S,13S,14S,16S,17S)-16-(3-Azido-propyl)-13-methyl-17-(tetrahydro-pyran-2-yloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yloxymethyl]-3-nitro-benzoic acid methyl ester (220810-55-9) → 4-[(8R,9S,13S,14S,16S,17S)-16-(3-Azido-propyl)-13-methyl-17-(tetrahydro-pyran-2-yloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yloxymethyl]-3-nitro-benzoic acid (220810-56-0)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/S0040-4039(98)02640-9

Reference yield:

4-bromomethyl-3-nitrobenzoic acid (55715-03-2) → 4-[(8R,9S,13S,14S,16S,17S)-16-(3-Azido-propyl)-13-methyl-17-(tetrahydro-pyran-2-yloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yloxymethyl]-3-nitro-benzoic acid (220810-56-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / benzene; methanol / Ambient temperature

2: 67 percent / CsCO₃ / acetonitrile; dimethylformamide / Ambient temperature

3: 83 percent / aq. LiOH / tetrahydrofuran / Ambient temperature

With lithium hydroxide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1016/S0040-4039(98)02640-9

Reference yield:

3-(O-tert-butyl(dimethyl)silyl)estrone (57711-40-7) → 4-[(8R,9S,13S,14S,16S,17S)-16-(3-Azido-propyl)-13-methyl-17-(tetrahydro-pyran-2-yloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yloxymethyl]-3-nitro-benzoic acid (220810-56-0)

Guidance literature:

Multi-step reaction with 8 steps

1: LDA / tetrahydrofuran / -78 °C

2: 1.) LDA, MeOH; 2.) LiAlH₄; 3.) p-TSA / 1.) THF, -78 deg C; 2.) THF, -78 deg C; 3.) CH₂Cl₂, r.t.

3: 79 percent / 1.) BH₃*THF; 2.) NaOH, H₂O₂ / 1.) 0 deg C

4: pyridine / 0 °C

5: NaN₃ / dimethylformamide / Ambient temperature

6: 98 percent / TBAF / tetrahydrofuran / 0 °C

7: 67 percent / CsCO₃ / acetonitrile; dimethylformamide / Ambient temperature

8: 83 percent / aq. LiOH / tetrahydrofuran / Ambient temperature

With pyridine; methanol; lithium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; sodium azide; borane-THF; tetrabutyl ammonium fluoride; dihydrogen peroxide; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(98)02640-9

upstream raw materials:

4-[(8R,9S,13S,14S,16S,17S)-16-(3-Azido-propyl)-13-methyl-17-(tetrahydro-pyran-2-yloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yloxymethyl]-3-nitro-benzoic acid methyl ester

4-bromomethyl-3-nitrobenzoic acid

3-(O-tert-butyl(dimethyl)silyl)estrone

(8R,9S,13S,14S,16R)-16-Allyl-3-(tert-butyl-dimethyl-silanyloxy)-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one