(2S,3S)-2-{(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}-6-methyl-6-triethylsilanyloxy-heptan-3-ol

Base Information

• Chemical Name: (2S,3S)-2-{(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}-6-methyl-6-triethylsilanyloxy-heptan-3-ol
• CAS No.: 161793-07-3
• Molecular Formula: C₄₅H₈₆O₄Si₃
• Molecular Weight: 775.432
• Mol file: 161793-07-3.mol

Synonyms:(2S,3S)-2-{(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}-6-methyl-6-triethylsilanyloxy-heptan-3-ol

Chemical Property of (2S,3S)-2-{(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}-6-methyl-6-triethylsilanyloxy-heptan-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-{(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}-6-methyl-6-triethylsilanyloxy-heptan-3-ol

There total 1 articles about (2S,3S)-2-{(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}-6-methyl-6-triethylsilanyloxy-heptan-3-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: 72.0%

(5Z,7E)-(1S,3R,20S)-1,3-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-22,23-dinor-5,7,10(19)-cholatrien-24-al (112924-91-1) + (3-bromo-1,1-dimethylpropoxy)triethylsilane (87417-12-7) → (2S,3S)-2-{(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}-6-methyl-6-triethylsilanyloxy-heptan-3-ol (161793-07-3)

Guidance literature:

(3-bromo-1,1-dimethylpropoxy)triethylsilane; With iodine; magnesium; In diethyl ether; at 20 - 40 ℃;

(5Z,7E)-(1S,3R,20S)-1,3-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-22,23-dinor-5,7,10(19)-cholatrien-24-al; In tetrahydrofuran; diethyl ether; at 0 - 20 ℃;

DOI:10.1016/S0968-0896(99)00249-7

Reference yield:

(2S,3S)-2-{(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}-6-methyl-6-triethylsilanyloxy-heptan-3-ol (161793-07-3) → (22R)-22,25-epoxy-1α-hydroxyvitamin D3

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 64 h / 4 °C

2: 63 percent / AG 50W-X₄ ion exchange resin; methanol / benzene / 13 h / 20 °C

With pyridine; methanol; AG 50W-X₄ ion exchange resin; In benzene; 1: Tosylation / 2: Substitution;

DOI:10.1016/S0968-0896(99)00249-7

Reference yield:

(2S,3S)-2-{(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}-6-methyl-6-triethylsilanyloxy-heptan-3-ol (161793-07-3) → (22R)-22-iodo-1α,25-dihydroxyvitamin D3

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 64 h / 4 °C

2: 8 percent / calcium carbonate; sodium iodide; mercury / acetone; butan-2-one / 80 h / 45 °C

3: 52 percent / AG 50W-X₄ ion exchange resin; methanol; mercury / benzene / 10 h / 20 °C

With pyridine; methanol; AG 50W-X₄ ion exchange resin; mercury; calcium carbonate; sodium iodide; In acetone; butanone; benzene; 1: Tosylation / 2: Substitution / 3: Substitution;

DOI:10.1016/S0968-0896(99)00249-7

upstream raw materials:

(5Z,7E)-(1S,3R,20S)-1,3-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-22,23-dinor-5,7,10(19)-cholatrien-24-al

(3-bromo-1,1-dimethylpropoxy)triethylsilane

Downstream raw materials:

Toluene-4-sulfonic acid (S)-1-((S)-1-{(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}-ethyl)-4-methyl-4-triethylsilanyloxy-pentyl ester

(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-((E)-1,5-dimethyl-5-triethylsilanyloxy-hex-1-enyl)-7a-methyl-octahydro-indene

(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-((1S,2R)-2-iodo-1,5-dimethyl-5-triethylsilanyloxy-hexyl)-7a-methyl-octahydro-indene

(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-((1S,2S)-2-iodo-1,5-dimethyl-5-triethylsilanyloxy-hexyl)-7a-methyl-octahydro-indene