(17E)-8β-<(tert-butyldimethylsilyl)oxy>-25-<(methoxymethyl)oxy>-16α-<(phenylcarbamoyl)oxy>-des-A,B-21-norcholest-17(20)-ene

Base Information

Chemical Name:(17E)-8β-<(tert-butyldimethylsilyl)oxy>-25-<(methoxymethyl)oxy>-16α-<(phenylcarbamoyl)oxy>-des-A,B-21-norcholest-17(20)-ene
CAS No.:217469-86-8
Molecular Formula:C₃₂H₅₃NO₅Si
Molecular Weight:559.862
Hs Code.:

Synonyms:(17E)-8β-<(tert-butyldimethylsilyl)oxy>-25-<(methoxymethyl)oxy>-16α-<(phenylcarbamoyl)oxy>-des-A,B-21-norcholest-17(20)-ene

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

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

There total 6 articles about (17E)-8β-<(tert-butyldimethylsilyl)oxy>-25-<(methoxymethyl)oxy>-16α-<(phenylcarbamoyl)oxy>-des-A,B-21-norcholest-17(20)-ene 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: 97.0%

: 103-71-9
phenyl isocyanate

: 217470-17-2
(17E)-8β-<(tert-butyldimethylsilyl)oxy>-25-<(methoxymethyl)oxy>-des-A,B-21-norcholest-17(20)-en-16α-ol

: 217469-86-8
(17E)-8β-<(tert-butyldimethylsilyl)oxy>-25-<(methoxymethyl)oxy>-16α-<(phenylcarbamoyl)oxy>-des-A,B-21-norcholest-17(20)-ene

Guidance literature:: With dmap; In tetrahydrofuran; at -10 ℃; for 12h;
DOI:10.1021/jo982393e

Reference yield:

: 2067-33-6
5-bromopentanoic acid

: 217469-86-8
(17E)-8β-<(tert-butyldimethylsilyl)oxy>-25-<(methoxymethyl)oxy>-16α-<(phenylcarbamoyl)oxy>-des-A,B-21-norcholest-17(20)-ene

Guidance literature:: Multi-step reaction with 6 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: 97 percent / DMAP / tetrahydrofuran / 12 h / -10 °C

With tert.-butylhydroperoxide; dmap; selenium(IV) oxide; potassium tert-butylate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jo982393e

Reference yield:

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

: 217469-86-8
(17E)-8β-<(tert-butyldimethylsilyl)oxy>-25-<(methoxymethyl)oxy>-16α-<(phenylcarbamoyl)oxy>-des-A,B-21-norcholest-17(20)-ene

Guidance literature:: Multi-step reaction with 5 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: 97 percent / DMAP / tetrahydrofuran / 12 h / -10 °C

With tert.-butylhydroperoxide; dmap; selenium(IV) oxide; potassium tert-butylate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo982393e