(22R)-des-A,B-8β-(benzoyloxy)-25-<(methoxymethyl)oxy>-22-<<(1'R)-3'-oxo-3'-<(methoxymethyl)oxy>-1'-methylpropyl>-oxy>cholest-23-yne

Base Information

Chemical Name:(22R)-des-A,B-8β-(benzoyloxy)-25-<(methoxymethyl)oxy>-22-<<(1'R)-3'-oxo-3'-<(methoxymethyl)oxy>-1'-methylpropyl>-oxy>cholest-23-yne
CAS No.:145354-35-4
Molecular Formula:C₃₃H₄₈O₈
Molecular Weight:572.739
Hs Code.:

Synonyms:(22R)-des-A,B-8β-(benzoyloxy)-25-<(methoxymethyl)oxy>-22-<<(1'R)-3'-oxo-3'-<(methoxymethyl)oxy>-1'-methylpropyl>-oxy>cholest-23-yne

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Chemical Property of (22R)-des-A,B-8β-(benzoyloxy)-25-<(methoxymethyl)oxy>-22-<<(1'R)-3'-oxo-3'-<(methoxymethyl)oxy>-1'-methylpropyl>-oxy>cholest-23-yne

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Technology Process of (22R)-des-A,B-8β-(benzoyloxy)-25-<(methoxymethyl)oxy>-22-<<(1'R)-3'-oxo-3'-<(methoxymethyl)oxy>-1'-methylpropyl>-oxy>cholest-23-yne

There total 7 articles about (22R)-des-A,B-8β-(benzoyloxy)-25-<(methoxymethyl)oxy>-22-<<(1'R)-3'-oxo-3'-<(methoxymethyl)oxy>-1'-methylpropyl>-oxy>cholest-23-yne 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%

: 107-30-2
chloromethyl methyl ether

: 145354-33-2
(22R)-des-A,B-8β-(benzoyloxy)-22<<(1'R)-2'-carboxy-1'-methylethyl>oxy>-23-cholestyn-25-ol

: 145354-35-4
(22R)-des-A,B-8β-(benzoyloxy)-25-<(methoxymethyl)oxy>-22-<<(1'R)-3'-oxo-3'-<(methoxymethyl)oxy>-1'-methylpropyl>-oxy>cholest-23-yne

Guidance literature:: With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 18h;
DOI:10.1021/jo00053a024

Reference yield:

: 66774-71-8
Benzoic acid (1R,3aR,4S,7aR)-7a-methyl-1-((S)-1-methyl-2-oxo-ethyl)-octahydro-inden-4-yl ester

: 145354-35-4
(22R)-des-A,B-8β-(benzoyloxy)-25-<(methoxymethyl)oxy>-22-<<(1'R)-3'-oxo-3'-<(methoxymethyl)oxy>-1'-methylpropyl>-oxy>cholest-23-yne

Guidance literature:: Multi-step reaction with 3 steps

1: 1) 2,6-di-tert-butylpyridine, 2a) TMSTf, 2b) Et₃N, MeOH / 1) CH₂Cl₂, -78 deg C, 5 min, 2a) -78 deg C, 2 h, 2b) -78 deg C, 5 min then to RT

2: TiCl₄ / CH₂Cl₂ / 12 h / -78 °C

3: 92 percent / DMAP, i-Pr₂NEt / CH₂Cl₂ / 18 h / 0 °C

With methanol; dmap; 2,6-di-tert-butyl-pyridine; TMSTf; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1021/jo00053a024

Reference yield:

: 55812-82-3,63730-57-4,63730-58-5,102281-42-5
(1R,3aR,4S,7aR)-7a-methyl-1-<(2E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl>-octahydro-1H-inden-4-ol

: 145354-35-4
(22R)-des-A,B-8β-(benzoyloxy)-25-<(methoxymethyl)oxy>-22-<<(1'R)-3'-oxo-3'-<(methoxymethyl)oxy>-1'-methylpropyl>-oxy>cholest-23-yne

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / DMAP, pyridine / 14 h / refrigerator

2: 95 percent / pyridine, ozone / methanol; CH₂Cl₂ / 0.42 h / -78 °C

3: 1) 2,6-di-tert-butylpyridine, 2a) TMSTf, 2b) Et₃N, MeOH / 1) CH₂Cl₂, -78 deg C, 5 min, 2a) -78 deg C, 2 h, 2b) -78 deg C, 5 min then to RT

4: TiCl₄ / CH₂Cl₂ / 12 h / -78 °C

5: 92 percent / DMAP, i-Pr₂NEt / CH₂Cl₂ / 18 h / 0 °C

With pyridine; methanol; dmap; 2,6-di-tert-butyl-pyridine; TMSTf; titanium tetrachloride; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;
DOI:10.1021/jo00053a024