3β-O-(tert-butyldimethylsilyl)-7,8-dihydroxy-7,8-dihydrovitamin D3

Base Information

• Chemical Name: 3β-O-(tert-butyldimethylsilyl)-7,8-dihydroxy-7,8-dihydrovitamin D3
• CAS No.: 84927-67-3
• Molecular Formula: C₃₃H₆₀O₃Si
• Molecular Weight: 532.923
• Mol file: 84927-67-3.mol

Synonyms:3β-O-(tert-butyldimethylsilyl)-7,8-dihydroxy-7,8-dihydrovitamin D3

Chemical Property of 3β-O-(tert-butyldimethylsilyl)-7,8-dihydroxy-7,8-dihydrovitamin D3

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3β-O-(tert-butyldimethylsilyl)-7,8-dihydroxy-7,8-dihydrovitamin D3

There total 2 articles about 3β-O-(tert-butyldimethylsilyl)-7,8-dihydroxy-7,8-dihydrovitamin D3 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: 86.0%

7,8-dihydroxy-7,8-dihydrovitamin D3 (84927-66-2) + tert-butyldimethylsilyl chloride (18162-48-6) → 3β-O-(tert-butyldimethylsilyl)-7,8-dihydroxy-7,8-dihydrovitamin D3 (84927-67-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 2h; Ambient temperature;

DOI:10.1021/jo00157a004

Reference yield:

vitamin D3 (67-97-0) → 3β-O-(tert-butyldimethylsilyl)-7,8-dihydroxy-7,8-dihydrovitamin D3 (84927-67-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / potassium permanganate / H₂O; ethanol / 1.) -10 deg C, 1 h, 2.) to 40 deg C, 10 min

2: 86 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

With 1H-imidazole; potassium permanganate; In ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00157a004

Reference yield:

3β-O-(tert-butyldimethylsilyl)-7,8-dihydroxy-7,8-dihydrovitamin D3 (84927-67-3) → 23-oxa-25-hydroxyvitamin D3 (84927-61-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) lead tetraacetate, 2.) Red-Al / 1.) benzene, pyridine, 25 deg C, 10 min, 2.) water, 1,5h

2: 91 percent / N-chlorosuccinimide, dimethyl sulfide / 1.) CH₂Cl₂, -20 deg C, 30 min, 2.) 0 deg C, 30 min

3: 1.) n-butyllithium, 2.) 5percent H₂O₂ / 1.) hexane, THF,-50 deg C, 15 min, 2.) chloroform, 1 min

4: 73 percent / n-butyllithium / tetrahydrofuran / 1.25 h / -78 deg C to room temp.

5: 61 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

6: 1.) mercuric acetate, 2.) 3M NaOH, sodium borohydride / 1.) THF, water, 0 deg C, 2.25 h

With lead(IV) acetate; sodium hydroxide; sodium tetrahydroborate; N-chloro-succinimide; n-butyllithium; dimethylsulfide; mercury(II) diacetate; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran;

DOI:10.1021/jo00157a004

upstream raw materials:

7,8-dihydroxy-7,8-dihydrovitamin D₃

tert-butyldimethylsilyl chloride

vitamin D₃

Downstream raw materials:

Grundmann's alcohol

(2Z)-2-<(5S)-5-(tert-butyldimethylsilyloxy)-2-methylene-cyclohexylidene>-ethanol

<(1Z),(5S)>-2-<5-(t-butyldimethylsilyl)oxy-2-methylenecyclohexylidene>-1-chloroethane

(S)-(Z)-{2-[5-(tert-butyldimethylsiloxy)-2-methylenecyclohexylidene]ethyl}diphenylphosphine oxide