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

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 methyl ester
CAS No.:220810-55-9
Molecular Formula:C₃₅H₄₄N₄O₇
Molecular Weight:632.757
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 methyl ester

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 methyl ester

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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 methyl ester

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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 methyl ester

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 methyl 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: 67.0%

: 88089-94-5
methyl 4-bromomethyl-3-nitrobenzoate

: 220810-54-8
3-(3-hydroxy-17β-(tetrahydro-2H-pyran-2-yl-oxy)-estra-1,3,5(10)-trien-16β-yl)-azidopropane

: 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

Guidance literature:: With CsCO₃; In N,N-dimethyl-formamide; acetonitrile; Ambient temperature;
DOI:10.1016/S0040-4039(98)02640-9

Reference yield:

: 53-16-7
Estrone

: 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

Guidance literature:: Multi-step reaction with 8 steps

1: imidazole / dimethylformamide / Ambient temperature

2: LDA / tetrahydrofuran / -78 °C

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

4: 79 percent / 1.) BH₃*THF; 2.) NaOH, H₂O₂ / 1.) 0 deg C

5: pyridine / 0 °C

6: NaN₃ / dimethylformamide / Ambient temperature

7: 98 percent / TBAF / tetrahydrofuran / 0 °C

8: 67 percent / CsCO₃ / acetonitrile; dimethylformamide / Ambient temperature

With pyridine; 1H-imidazole; methanol; 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

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 2 steps

1: 96 percent / benzene; methanol / Ambient temperature

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

With CsCO₃; In methanol; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1016/S0040-4039(98)02640-9