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
Hs Code.:

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

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

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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

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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%

: 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 methyl ester

: 220810-56-0
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

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; Ambient temperature;
DOI:10.1016/S0040-4039(98)02640-9

Reference yield:

: 55715-03-2
4-bromomethyl-3-nitrobenzoic acid

: 220810-56-0
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

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:

: 57711-40-7
3-(O-tert-butyl(dimethyl)silyl)estrone

: 220810-56-0
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

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