((4S,5S)-5-((S,E)-6-((tert-butyldiphenylsilyl)oxy)-4-methylhex-1-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol

Base Information

• Chemical Name: ((4S,5S)-5-((S,E)-6-((tert-butyldiphenylsilyl)oxy)-4-methylhex-1-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol
• CAS No.: 1199807-70-9
• Molecular Formula: C₂₉H₄₂O₄Si
• Molecular Weight: 482.736
• Mol file: 1199807-70-9.mol

Synonyms:((4S,5S)-5-((S,E)-6-((tert-butyldiphenylsilyl)oxy)-4-methylhex-1-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol

Chemical Property of ((4S,5S)-5-((S,E)-6-((tert-butyldiphenylsilyl)oxy)-4-methylhex-1-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((4S,5S)-5-((S,E)-6-((tert-butyldiphenylsilyl)oxy)-4-methylhex-1-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol

There total 9 articles about ((4S,5S)-5-((S,E)-6-((tert-butyldiphenylsilyl)oxy)-4-methylhex-1-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol 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: 100.0%

tert-butyl(((S,E)-6-((4S,5S)-5-(((4-methoxybenzyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-methylhex-5-en-1-yl)oxy)diphenylsilane (1313511-79-3) → ((4S,5S)-5-((S,E)-6-((tert-butyldiphenylsilyl)oxy)-4-methylhex-1-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol (1199807-70-9)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃;

DOI:10.1039/c0ob01253j

Reference yield: 72.0%

(S)-tert-butyl(3-methylhex-5-enyloxy)diphenylsilane (1199807-60-7) + (S,S)-2,2-dimethyl-4-[(tert-butyldimethylsilyloxy)methyl]-5-vinyl-1,3-dioxolane (207123-21-5) → ((4S,5S)-5-((S,E)-6-((tert-butyldiphenylsilyl)oxy)-4-methylhex-1-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol (1199807-70-9)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 12h; Reflux; Inert atmosphere;

DOI:10.1021/ol9025183

Reference yield:

(S)-5-(tert-butyldiphenylsilyloxy)-3-methylpentan-1-ol (1046471-35-5) → ((4S,5S)-5-((S,E)-6-((tert-butyldiphenylsilyl)oxy)-4-methylhex-1-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol (1199807-70-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C

2.1: ammonium molybdate(VI) tetrahydrate; dihydrogen peroxide / ethanol; water / 0 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C

3.2: 6.25 h / -78 °C

4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 20 °C

With ammonium molybdate(VI) tetrahydrate; di-isopropyl azodicarboxylate; dihydrogen peroxide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; water; 1.1: Mitsunobu reaction / 3.1: Julia-Kocienski olefination / 3.2: Julia-Kocienski olefination;

DOI:10.1039/c0ob01253j

upstream raw materials:

(S)-tert-butyl(3-methylhex-5-enyloxy)diphenylsilane

(S,S)-2,2-dimethyl-4-[(tert-butyldimethylsilyloxy)methyl]-5-vinyl-1,3-dioxolane

(S)-5-(tert-butyldiphenylsilyloxy)-3-methylpentan-1-ol

(R)-5-((5-((tert-butyldiphenylsilyl)oxy)-3-methylpentyl)sulfonyl)-1-phenyl-1H-tetrazole

Downstream raw materials:

tert-butyl(((S,E)-6-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-3-methylhex-5-en-1-yl)oxy)diphenylsilane