(5Z,7E)-(1S,3R)-1,3-dihydroxy-23a-homo-9,10-secochola-5,7,10⁽¹⁹⁾-trien-24-oic acid methyl ester

Base Information

• Chemical Name: (5Z,7E)-(1S,3R)-1,3-dihydroxy-23a-homo-9,10-secochola-5,7,10⁽¹⁹⁾-trien-24-oic acid methyl ester
• CAS No.: 74029-72-4
• Molecular Formula: C₂₆H₄₀O₄
• Molecular Weight: 416.601
• Mol file: 74029-72-4.mol

Synonyms:(5Z,7E)-(1S,3R)-1,3-dihydroxy-23a-homo-9,10-secochola-5,7,10⁽¹⁹⁾-trien-24-oic acid methyl ester

Chemical Property of (5Z,7E)-(1S,3R)-1,3-dihydroxy-23a-homo-9,10-secochola-5,7,10⁽¹⁹⁾-trien-24-oic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5Z,7E)-(1S,3R)-1,3-dihydroxy-23a-homo-9,10-secochola-5,7,10⁽¹⁹⁾-trien-24-oic acid methyl ester

There total 1 articles about (5Z,7E)-(1S,3R)-1,3-dihydroxy-23a-homo-9,10-secochola-5,7,10⁽¹⁹⁾-trien-24-oic acid methyl ester 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: 96.0%

(R)-5-{(1R,3aS,7aR)-4-[2-[(3S,5R)-5-Acetoxy-3-hydroxy-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-hexanoic acid methyl ester → (5Z,7E)-(1S,3R)-1,3-dihydroxy-23a-homo-9,10-secochola-5,7,10(19)-trien-24-oic acid methyl ester (74029-72-4)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; methanol; for 3h; Ambient temperature;

DOI:10.1016/S0039-128X(97)00040-8

Reference yield: 93.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (5Z,7E)-(1S,3R)-1,3-dihydroxy-23a-homo-9,10-secochola-5,7,10(19)-trien-24-oic acid methyl ester (74029-72-4) → 1α-[(tert-butyldimethylsilyl)oxy]-24-(methoxycarbonyl)-25,26,27-trisnorvitamin D3 tert-butyldimethylsilyl ether (145372-43-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 2.5h; Ambient temperature;

DOI:10.1016/S0039-128X(97)00040-8

Reference yield:

(5Z,7E)-(1S,3R)-1,3-dihydroxy-23a-homo-9,10-secochola-5,7,10(19)-trien-24-oic acid methyl ester (74029-72-4) → (R)-5-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-hexan-1-ol (194232-09-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / imidazole / dimethylformamide / 2.5 h / Ambient temperature

2: 91 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / Ambient temperature

With 1H-imidazole; lithium aluminium tetrahydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0039-128X(97)00040-8

Downstream raw materials:

1α-[(tert-butyldimethylsilyl)oxy]-24-(methoxycarbonyl)-25,26,27-trisnorvitamin D3 tert-butyldimethylsilyl ether

PRI-1890

(R)-5-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-hexan-1-ol

(R)-5-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-hexanal