(22R,23Z)-de-A,B-8β-(benzoyloxy)-25-<(methoxymethyl)oxy>cholest-23-en-ol

Base Information

• Chemical Name: (22R,23Z)-de-A,B-8β-(benzoyloxy)-25-<(methoxymethyl)oxy>cholest-23-en-ol
• CAS No.: 100858-22-8
• Molecular Formula: C₂₇H₄₀O₅
• Molecular Weight: 444.612
• Mol file: 100858-22-8.mol

Synonyms:(22R,23Z)-de-A,B-8β-(benzoyloxy)-25-<(methoxymethyl)oxy>cholest-23-en-ol

Chemical Property of (22R,23Z)-de-A,B-8β-(benzoyloxy)-25-<(methoxymethyl)oxy>cholest-23-en-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (22R,23Z)-de-A,B-8β-(benzoyloxy)-25-<(methoxymethyl)oxy>cholest-23-en-ol

There total 1 articles about (22R,23Z)-de-A,B-8β-(benzoyloxy)-25-<(methoxymethyl)oxy>cholest-23-en-ol 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:

de-A,B-8β-(benzoyloxy)-25-<(methoxymethyl)oxy>cholest-23-yn-22-ol (100858-20-6,100937-69-7) → (22S,23Z)-de-A,B-8β-(benzoyloxy)-25-<(methoxymethyl)oxy>cholest-23-en-ol (100937-70-0) + (22R,23Z)-de-A,B-8β-(benzoyloxy)-25-<(methoxymethyl)oxy>cholest-23-en-ol (100858-22-8)

Guidance literature:

With quinoline; hydrogen; Pd-BaSO₄; In methanol; for 0.133333h; under 93.09 Torr; Yield given. Yields of byproduct given;

DOI:10.1021/jo00358a018

Reference yield: 95.0%

phenyl isocyanate (103-71-9) + (22R,23Z)-de-A,B-8β-(benzoyloxy)-25-<(methoxymethyl)oxy>cholest-23-en-ol (100858-22-8) → (22R,23Z)-de-A,B-8β-(benzoyloxy)-25-<(methoxymethyl)oxy>-22-<(phenylcarbamoyl)oxy>cholest-23-ene (100858-23-9)

Guidance literature:

With pyridine; dmap; at 0 ℃;

DOI:10.1021/jo00358a018

Reference yield:

(22R,23Z)-de-A,B-8β-(benzoyloxy)-25-<(methoxymethyl)oxy>cholest-23-en-ol (100858-22-8) → ercalcidiol (21343-40-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / (4-dimethylamino)pyridine (DMAP), pyridine / 0 °C

2: 1.) Cu₂I₂ / 1.) Et₂O, 0 deg C, 30 min, 2.) Et₂O, RT, 48 h

3: 100 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

4: 100 percent / pyridinium dichromate, pyridinium p-toluenesulfonate / CH₂Cl₂ / 24 h / Ambient temperature

5: 1.) n-BuLi / 1.) hexane, THF, -70 deg C, 30 min, 2.) THF, -70 deg C, 90 min

6: 76 percent / AG-50WX₄(resin) / methanol / 16 h / Ambient temperature

With pyridine; dmap; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; copper (I) iodide; AG-50WX₄(resin); pyridinium p-toluenesulfonate; In methanol; diethyl ether; dichloromethane;

DOI:10.1021/jo00358a018

upstream raw materials:

de-A,B-8β-(benzoyloxy)-25-<(methoxymethyl)oxy>cholest-23-yn-22-ol

Downstream raw materials:

(22R,23Z)-de-A,B-8β-(benzoyloxy)-25-<(methoxymethyl)oxy>-22-<(phenylcarbamoyl)oxy>cholest-23-ene

ercalcidiol

(22E,24S)-de-A,B-25-<(methoxymethyl)oxy>ergost-22-en-8-one

25-<(methoxymethyl)oxy>vitamin D2 tert-butyldimethylsilyl ether