(17E)-25-<(methoxymethyl)oxy>-16α-<(phenylcarbamoyl)oxy>-des-A,B-21-norcholest-17(20)-en-8-one

Base Information

Chemical Name:(17E)-25-<(methoxymethyl)oxy>-16α-<(phenylcarbamoyl)oxy>-des-A,B-21-norcholest-17(20)-en-8-one
CAS No.:228420-75-5
Molecular Formula:C₂₆H₃₇NO₅
Molecular Weight:443.583
Hs Code.:

Synonyms:(17E)-25-<(methoxymethyl)oxy>-16α-<(phenylcarbamoyl)oxy>-des-A,B-21-norcholest-17(20)-en-8-one

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Chemical Property of (17E)-25-<(methoxymethyl)oxy>-16α-<(phenylcarbamoyl)oxy>-des-A,B-21-norcholest-17(20)-en-8-one

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Technology Process of (17E)-25-<(methoxymethyl)oxy>-16α-<(phenylcarbamoyl)oxy>-des-A,B-21-norcholest-17(20)-en-8-one

There total 7 articles about (17E)-25-<(methoxymethyl)oxy>-16α-<(phenylcarbamoyl)oxy>-des-A,B-21-norcholest-17(20)-en-8-one 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: 92.0%

: 228420-94-8
(17E)-25-<(methoxymethyl)oxy>-16α-<(phenylcarbamoyl)oxy>-des-A,B-21-norcholest-17(20)-en-8β-ol

: 228420-75-5
(17E)-25-<(methoxymethyl)oxy>-16α-<(phenylcarbamoyl)oxy>-des-A,B-21-norcholest-17(20)-en-8-one

Guidance literature:: With dipyridinium dichromate; pyridinium p-toluenesulfonate; In dichloromethane; for 6h;
DOI:10.1021/jo982393e

Reference yield:

: 2067-33-6
5-bromopentanoic acid

: 228420-75-5
(17E)-25-<(methoxymethyl)oxy>-16α-<(phenylcarbamoyl)oxy>-des-A,B-21-norcholest-17(20)-en-8-one

Guidance literature:: Multi-step reaction with 8 steps

1: 96 percent / acetonitrile / 24 h / 80 °C

2: 1.) t-BuOK / 1.) C₆H₆, reflux, 2 h, 2.) C₆H₆, 80 deg C, 36 h

3: 1.) THF, Et₂O, room temperature, 12 h, 2) THF, Et₂O, -78 deg C, 3 h; -78 deg C to room temperature, 3 h

4: 92 percent / DMAP, i-Pr₂NEt / CH₂Cl₂ / 24 h / 0 °C

5: 90 percent / t-BuOOH, SeO₂ / CH₂Cl₂ / 6 h / Ambient temperature

6: 99 percent / TBAF / tetrahydrofuran / 24 h / Heating

7: 89 percent / DMAP / pyridine / 20 h / -25 °C

8: 92 percent / PDC, PPTS / CH₂Cl₂ / 6 h

With tert.-butylhydroperoxide; dmap; dipyridinium dichromate; selenium(IV) oxide; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; dichloromethane; acetonitrile;
DOI:10.1021/jo982393e

Reference yield:

: 17814-85-6
(4-carboxybutyl)triphenylphosphonium bromide

: 228420-75-5
(17E)-25-<(methoxymethyl)oxy>-16α-<(phenylcarbamoyl)oxy>-des-A,B-21-norcholest-17(20)-en-8-one

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) t-BuOK / 1.) C₆H₆, reflux, 2 h, 2.) C₆H₆, 80 deg C, 36 h

2: 1.) THF, Et₂O, room temperature, 12 h, 2) THF, Et₂O, -78 deg C, 3 h; -78 deg C to room temperature, 3 h

3: 92 percent / DMAP, i-Pr₂NEt / CH₂Cl₂ / 24 h / 0 °C

4: 90 percent / t-BuOOH, SeO₂ / CH₂Cl₂ / 6 h / Ambient temperature

5: 99 percent / TBAF / tetrahydrofuran / 24 h / Heating

6: 89 percent / DMAP / pyridine / 20 h / -25 °C

7: 92 percent / PDC, PPTS / CH₂Cl₂ / 6 h

With tert.-butylhydroperoxide; dmap; dipyridinium dichromate; selenium(IV) oxide; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; dichloromethane;
DOI:10.1021/jo982393e