20S-Hydroxyvitamin D₃

Base Information

• Chemical Name: 20S-Hydroxyvitamin D₃
• CAS No.: 651734-12-2
• Molecular Formula: C₂₇H₄₄O₂
• Molecular Weight: 400.645
• Mol file: 651734-12-2.mol

Synonyms:20S-Hydroxyvitamin D₃

Chemical Property of 20S-Hydroxyvitamin D₃

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 20S-Hydroxyvitamin D₃

There total 29 articles about 20S-Hydroxyvitamin 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: 37.0%

tert-butyl(((1S,Z)-3-((E)-2-((1S,7aS)-1-((S)-2-(ethoxymethoxy)-6-methylheptan-2-yl)-7a-methylhexahydro-1H-inden-4(2H)-ylidene)ethylidene)-4-methylenecyclohexyl)oxy)dimethylsilane → 20S-Hydroxyvitamin D3 (651734-12-2)

Guidance literature:

With camphor-10-sulfonic acid; sodium hydrogencarbonate; In methanol; dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/j.steroids.2015.09.009

Reference yield:

(2Z)-2-<(5S)-5-(tert-butyldimethylsilyloxy)-2-methylene-cyclohexylidene>-ethanol (96685-53-9) → 20S-Hydroxyvitamin D3 (651734-12-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / 0 °C / Inert atmosphere

1.2: 5 h / 0 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere

3.1: dihydrogen peroxide / dichloromethane / 0 °C

4.1: phenyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

4.2: 15 h / -78 °C / Inert atmosphere

5.1: camphor-10-sulfonic acid; sodium hydrogencarbonate / methanol; dichloromethane / 3 h / 20 °C

With n-butyllithium; camphor-10-sulfonic acid; dihydrogen peroxide; sodium hydrogencarbonate; phenyllithium; In tetrahydrofuran; methanol; hexane; dichloromethane;

DOI:10.1016/j.steroids.2015.09.009

Reference yield:

(1S,4S,7aS)-1-cetyl-7a-methyloctahydro-1H-inden-4-yl acetate (154314-43-9) → 20S-Hydroxyvitamin D3 (651734-12-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: magnesium / tetrahydrofuran / 20 °C / Inert atmosphere; Reflux

1.2: 20 °C / Inert atmosphere

2.1: dipyridinium dichromate / dichloromethane / 1 h / 20 °C

3.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Cooling with ice

4.1: phenyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

4.2: 15 h / -78 °C / Inert atmosphere

5.1: camphor-10-sulfonic acid; sodium hydrogencarbonate / methanol; dichloromethane / 3 h / 20 °C

With dmap; dipyridinium dichromate; camphor-10-sulfonic acid; sodium hydrogencarbonate; magnesium; phenyllithium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane;

DOI:10.1016/j.steroids.2015.09.009

upstream raw materials:

C₂₉H₄₆O₃

vitamin D₃

(1R,3aR,4S,7aR)-7a-methyl-1-<(2E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl>-octahydro-1H-inden-4-ol

Calciferol

Downstream raw materials:

1α,20,24-trihydroxyvitamin D₃

1α,20,25-trihydroxyvitamin D₃

1alpha,20-Dihydroxyvitamin D₃

20,25-dihydroxyvitamin D₃

Refernces

• 1、 Wang, Qinghui,Lin, Zongtao,Kim, Tae-Kang,Slominski, Andrzej T.,Miller, Duane D.,Li, Wei. "Total synthesis of biologically active 20S-hydroxyvitamin D3". . p. 153 - 162. Retrieved 2015/12/01.
• 2、 Tang, Edith K.Y.,Chen, Jianjun,Janjetovic, Zorica,Tieu, Elaine W.,Slominski, Andrzej T.,Li, Wei,Tuckey, Robert C.. "Hydroxylation of CYP11A1-derived products of vitamin D3 metabolism by human and Mouse CYP27B1". . p. 1112 - 1124. Retrieved 2013/07/19.