3β-methoxy-20α-[4-nitro-3-{1'-(p-nitrophenoxycarbonyloxy)ethyl}-phenoxymethyl]-5-pregnen

Base Information

Chemical Name:3β-methoxy-20α-[4-nitro-3-{1'-(p-nitrophenoxycarbonyloxy)ethyl}-phenoxymethyl]-5-pregnen
CAS No.:442853-31-8
Molecular Formula:C₃₈H₄₈N₂O₉
Molecular Weight:676.807
Hs Code.:

Synonyms:3β-methoxy-20α-[4-nitro-3-{1'-(p-nitrophenoxycarbonyloxy)ethyl}-phenoxymethyl]-5-pregnen

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Chemical Property of 3β-methoxy-20α-[4-nitro-3-{1'-(p-nitrophenoxycarbonyloxy)ethyl}-phenoxymethyl]-5-pregnen

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Technology Process of 3β-methoxy-20α-[4-nitro-3-{1'-(p-nitrophenoxycarbonyloxy)ethyl}-phenoxymethyl]-5-pregnen

There total 7 articles about 3β-methoxy-20α-[4-nitro-3-{1'-(p-nitrophenoxycarbonyloxy)ethyl}-phenoxymethyl]-5-pregnen 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: 59.4%

: 7693-46-1
4-Nitrophenyl chloroformate

: 442853-30-7
20α-[3-(1'-hydroxyethyl)-4-nitrophenoxymethyl]-3β-methoxy-5-pregnen

: 442853-31-8
3β-methoxy-20α-[4-nitro-3-{1'-(p-nitrophenoxycarbonyloxy)ethyl}-phenoxymethyl]-5-pregnen

Guidance literature:: With dmap; In chloroform; at 20 ℃;
DOI:10.1016/S0040-4020(02)00077-7

Reference yield:

: 1778-02-5
Pregnenolone acetate

: 442853-31-8
3β-methoxy-20α-[4-nitro-3-{1'-(p-nitrophenoxycarbonyloxy)ethyl}-phenoxymethyl]-5-pregnen

Guidance literature:: Multi-step reaction with 7 steps

1.1: t-BuOK / tetrahydrofuran / 12 h / Heating

1.2: 94.7 percent / K₂CO₃ / methanol / 15 h / 20 °C

2.1: 88 percent / KOH / dimethylsulfoxide / 10 h / 20 °C

3.1: 9-BBN / tetrahydrofuran / 13 h / Heating

3.2: 89.6 percent / 2N NaOH; 30 percent H₂O₂ / tetrahydrofuran / 16 h / 0 - 20 °C

4.1: 96 percent / pyridine / 12 h / 0 - 20 °C

5.1: 71.6 percent / K₂CO₃ / dimethylformamide / 110 °C

6.1: 91 percent / NaBH₄ / ethanol / 20 °C

7.1: 59.4 percent / DMAP / CHCl₃ / 20 °C

With dmap; potassium hydroxide; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; potassium tert-butylate; potassium carbonate; In tetrahydrofuran; pyridine; ethanol; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide; 1.1: Wittig reaction;
DOI:10.1016/S0040-4020(02)00077-7

Reference yield:

: 17879-91-3
(3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-(prop-1-en-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

: 442853-31-8
3β-methoxy-20α-[4-nitro-3-{1'-(p-nitrophenoxycarbonyloxy)ethyl}-phenoxymethyl]-5-pregnen

Guidance literature:: Multi-step reaction with 6 steps

1.1: 88 percent / KOH / dimethylsulfoxide / 10 h / 20 °C

2.1: 9-BBN / tetrahydrofuran / 13 h / Heating

2.2: 89.6 percent / 2N NaOH; 30 percent H₂O₂ / tetrahydrofuran / 16 h / 0 - 20 °C

3.1: 96 percent / pyridine / 12 h / 0 - 20 °C

4.1: 71.6 percent / K₂CO₃ / dimethylformamide / 110 °C

5.1: 91 percent / NaBH₄ / ethanol / 20 °C

6.1: 59.4 percent / DMAP / CHCl₃ / 20 °C

With dmap; potassium hydroxide; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; potassium carbonate; In tetrahydrofuran; pyridine; ethanol; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(02)00077-7