Silane, [[(1R,3R)-5-(2-chloroethylidene)-1,3-cyclohexanediyl]bis(oxy)]bis[(1,1-dimethylethyl)dimethyl-

Base Information

• Chemical Name: Silane, [[(1R,3R)-5-(2-chloroethylidene)-1,3-cyclohexanediyl]bis(oxy)]bis[(1,1-dimethylethyl)dimethyl-
• CAS No.: 139356-38-0
• Molecular Formula: C₂₀H₄₁ClO₂Si₂
• Molecular Weight: 405.168
• DSSTox Substance ID: DTXSID201112585
• Mol file: 139356-38-0.mol

Synonyms:139356-38-0;Silane, [[(1R,3R)-5-(2-chloroethylidene)-1,3-cyclohexanediyl]bis(oxy)]bis[(1,1-dimethylethyl)dimethyl-;tert-butyl-[(1R,3R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-chloroethylidene)cyclohexyl]oxy-dimethylsilane;Paricalcitol Impurity B01;(((1R,3R)-5-(2-chloroethylidene)cyclohexane-1,3-diyl)bis(oxy)) bis(tert-butyldimethylsilane);DTXSID201112585

Chemical Property of Silane, [[(1R,3R)-5-(2-chloroethylidene)-1,3-cyclohexanediyl]bis(oxy)]bis[(1,1-dimethylethyl)dimethyl-

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 404.2333613
• Heavy Atom Count: 25
• Complexity: 435

Purity/Quality:

NLT 98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OC1CC(CC(=CCCl)C1)O[Si](C)(C)C(C)(C)C
• Isomeric SMILES: CC(C)(C)[Si](C)(C)O[C@H]1C[C@@H](CC(=CCCl)C1)O[Si](C)(C)C(C)(C)C

Technology Process of Silane, [[(1R,3R)-5-(2-chloroethylidene)-1,3-cyclohexanediyl]bis(oxy)]bis[(1,1-dimethylethyl)dimethyl-

There total 25 articles about Silane, [[(1R,3R)-5-(2-chloroethylidene)-1,3-cyclohexanediyl]bis(oxy)]bis[(1,1-dimethylethyl)dimethyl- 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:

[(3R,5R)-3,5-bis-(tert-butyldimethylsilanyloxy)cyclohexylidene]-ethanol (139356-37-9) + methanesulfonyl chloride (124-63-0) → ((1R,3R)-5-(2-chloroethylidene)cyclohexane-1,3-diyl)bis(oxy)bis(tert-butyldimethylsilane) (139356-38-0)

Guidance literature:

With pyridine; lithium chloride; In N,N-dimethyl-formamide; at 0 ℃; for 2h;

Reference yield:

3,5-di-(tert-butyl-dimethylsilyloxy)-(3S,5S)-cyclohexan-1-one (139356-35-7) → ((1R,3R)-5-(2-chloroethylidene)cyclohexane-1,3-diyl)bis(oxy)bis(tert-butyldimethylsilane) (139356-38-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / LDA / tetrahydrofuran / 2 h / -78 °C

2: DIBAL-H / toluene / 1 h / -78 °C

3: 80 percent / N-chlorosuccinimide-dimethylsulfide complex / CH₂Cl₂ / -25 - 0 °C

With N-chlorosuccinimide-dimethylsulfide; diisobutylaluminium hydride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/0040-4039(91)80559-O

Reference yield:

(3S,5S)-3,5-bis[tert-butyl(dimethyl)silyloxy]-1-(hydroxylmethyl)cyclohexanol (139356-34-6) → ((1R,3R)-5-(2-chloroethylidene)cyclohexane-1,3-diyl)bis(oxy)bis(tert-butyldimethylsilane) (139356-38-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / satd. NaIO₄ / H₂O; methanol / 0.5 h / 0 °C

2: 86 percent / LDA / tetrahydrofuran / 2 h / -78 °C

3: DIBAL-H / toluene / 1 h / -78 °C

4: 80 percent / N-chlorosuccinimide-dimethylsulfide complex / CH₂Cl₂ / -25 - 0 °C

With sodium periodate; N-chlorosuccinimide-dimethylsulfide; diisobutylaluminium hydride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; toluene;

DOI:10.1016/0040-4039(91)80559-O

upstream raw materials:

(R)-7-Benzyloxy-5-methylene-heptane-1,3-diol

(R)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methylene-heptanal

(R)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methylene-heptan-1-ol

(1R,5R)-3-[2-Benzyloxy-eth-(Z)-ylidene]-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol

Downstream raw materials:

1α,25-dihydroxy-19-nor-vitamin D₃

(1R,7aR)-4-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-1-((R)-1,5-dimethyl-5-trimethylsilanyloxy-hexyl)-7a-methyl-octahydro-indene

((1R,3R)-5-((E)-2-((1R,3aS,7aR)-1-((S)-1,1-dimethoxypropan-2-yl)-7a-methyldihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)cyclohexane-1,3-diyl)bis(oxy)bis(tertbutyldimethylsilane)

(S)-2-((1R,3aS,7aR,E)-4-(2-((3R,5R)-3,5-bis(tertbutyldimethylsilyloxy)cyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)propanal

Refernces

• 1、 Samala, Ramakrishna,Sharma, Somesh,Basu, Manas K.,Mukkanti,Porstmann, Frank. "A new metabolite of Paricalcitol: stereoselective synthesis of (22Z)-isomer of 1α,25-dihydroxy-19-norvitamin D2". . p. 1309 - 1312. Retrieved 2018/03/26.
• 2、 Courtney, Lawrence F.,Lange, Meinolf,Uskokovic, Milan R.,Wovkulich, Peter M.. "Asymmetric synthesis of a key ring a synthon for 1α-hydroxy-19-nor vitamin D". . p. 3363 - 3366. Retrieved 2007/10/03.