De-A,B-24-oxo-23,25-(isopropylidenedioxy)cholestan-8-benzyloxymethyl ether

Base Information

Chemical Name:De-A,B-24-oxo-23,25-(isopropylidenedioxy)cholestan-8-benzyloxymethyl ether
CAS No.:271796-46-4
Molecular Formula:C₂₉H₄₄O₅
Molecular Weight:472.665
Hs Code.:

Synonyms:De-A,B-24-oxo-23,25-(isopropylidenedioxy)cholestan-8-benzyloxymethyl ether

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Chemical Property of De-A,B-24-oxo-23,25-(isopropylidenedioxy)cholestan-8-benzyloxymethyl ether

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Technology Process of De-A,B-24-oxo-23,25-(isopropylidenedioxy)cholestan-8-benzyloxymethyl ether

There total 9 articles about De-A,B-24-oxo-23,25-(isopropylidenedioxy)cholestan-8-benzyloxymethyl ether 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: 78.0%

: 77-76-9
2,2-dimethoxy-propane

: 189894-15-3
De-A,B-24-oxo-23,25-dihydroxy-cholestan-8-benzyloxymethyl ether

: 271796-46-4
De-A,B-24-oxo-23,25-(isopropylidenedioxy)cholestan-8-benzyloxymethyl ether

Guidance literature:: With pyridinium p-toluenesulfonate; In N,N-dimethyl-formamide; for 48h;
DOI:10.1016/S0039-128X(99)00110-5

Reference yield:

: 64190-52-9
(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol

: 271796-46-4
De-A,B-24-oxo-23,25-(isopropylidenedioxy)cholestan-8-benzyloxymethyl ether

Guidance literature:: Multi-step reaction with 9 steps

1.1: 97 percent / Ph₃P; imidazole; I₂ / benzene / 3 h / 20 °C

2.1: 94 percent / dimethylformamide

3.1: 100 percent / Hunig's base / CH₂Cl₂ / 20 °C

4.1: diisopropylamine; tetramethylenediamine; n-BuLi / tetrahydrofuran; hexane / 0.25 h / -20 °C

4.2: 81 percent / tetrahydrofuran; hexane / 5 h

5.1: 86 percent / 5 percent Na/Hg; Na₂HPO₄ / methanol / 1 h / 0 °C

6.1: 71 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2.25 h / -78 - -10 °C

7.1: LDA / tetrahydrofuran; hexane / 0.08 h / -20 °C

7.2: tetrahydrofuran; hexane / 3.5 h / 0 °C

8.1: chloroperbenzoic acid / CH₂Cl₂ / 4 h / 0 °C

9.1: 78 percent / pyridinium p-toluenesulfonate / dimethylformamide / 48 h

With 1H-imidazole; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; iodine; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; benzene; 1.1: Iodination / 2.1: sulfonylation / 3.1: Etherification / 4.1: Metallation / 4.2: Ring cleavage / 5.1: Hydrogenolysis / 6.1: Oxidation / 7.1: Metallation / 7.2: silylation / 8.1: Oxidation / 9.1: ketalization;
DOI:10.1016/S0039-128X(99)00110-5

Reference yield:

: 116535-65-0
(1R,3aR,4S,7aR)-octahydro-1-[(S)-1-iodopropan-2-yl]-7a-methyl-1H-inden-4-ol

: 271796-46-4
De-A,B-24-oxo-23,25-(isopropylidenedioxy)cholestan-8-benzyloxymethyl ether

Guidance literature:: Multi-step reaction with 8 steps

1.1: 94 percent / dimethylformamide

2.1: 100 percent / Hunig's base / CH₂Cl₂ / 20 °C

3.1: diisopropylamine; tetramethylenediamine; n-BuLi / tetrahydrofuran; hexane / 0.25 h / -20 °C

3.2: 81 percent / tetrahydrofuran; hexane / 5 h

4.1: 86 percent / 5 percent Na/Hg; Na₂HPO₄ / methanol / 1 h / 0 °C

5.1: 71 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2.25 h / -78 - -10 °C

6.1: LDA / tetrahydrofuran; hexane / 0.08 h / -20 °C

6.2: tetrahydrofuran; hexane / 3.5 h / 0 °C

7.1: chloroperbenzoic acid / CH₂Cl₂ / 4 h / 0 °C

8.1: 78 percent / pyridinium p-toluenesulfonate / dimethylformamide / 48 h

With disodium hydrogenphosphate; sodium amalgam; n-butyllithium; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: sulfonylation / 2.1: Etherification / 3.1: Metallation / 3.2: Ring cleavage / 4.1: Hydrogenolysis / 5.1: Oxidation / 6.1: Metallation / 6.2: silylation / 7.1: Oxidation / 8.1: ketalization;
DOI:10.1016/S0039-128X(99)00110-5