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

Base Information

• Chemical Name: (S,S)-2,2-dimethyl-4-[(tert-butyldimethylsilyloxy)methyl]-5-vinyl-1,3-dioxolane
• CAS No.: 207123-21-5
• Molecular Formula: C₈H₁₄O₃
• Molecular Weight: 158.197
• Mol file: 207123-21-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (S,S)-2,2-dimethyl-4-[(tert-butyldimethylsilyloxy)methyl]-5-vinyl-1,3-dioxolane 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:

(4R,5R)-2,2-Dimethyl-5-vinyl-1,3-dioxolan-4-carbonsaeure-methylester (85963-83-3) → (4S,5R)-2,2-dimethyl-4-hydroxymethyl-5-vinyl-1,3-dioxolane (114817-96-8,127758-25-2,99902-67-7) + (S,S)-2,2-dimethyl-4-[(tert-butyldimethylsilyloxy)methyl]-5-vinyl-1,3-dioxolane (207123-21-5)

Guidance literature:

With diisobutylaluminium hydride; In diethyl ether; hexane; Yield given. Yields of byproduct given. Title compound not separated from byproducts; -75 deg C, 30 min; r.t., 1.5 h;

Reference yield: 95.0%

(S,S)-2,2-dimethyl-4-[(tert-butyldimethylsilyloxy)methyl]-5-vinyl-1,3-dioxolane (207123-21-5) + p-toluenesulfonyl chloride (98-59-9) → [(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methyl 4-methyl-benzenesulfonate (121469-49-6)

Guidance literature:

(S,S)-2,2-dimethyl-4-[(tert-butyldimethylsilyloxy)methyl]-5-vinyl-1,3-dioxolane; p-toluenesulfonyl chloride; With triethylamine; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

With dmap; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1002/ejoc.201300434

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

upstream raw materials:

(4R,5R)-2,2-Dimethyl-5-vinyl-1,3-dioxolan-4-carbonsaeure-methylester

Downstream raw materials:

[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methyl 4-methyl-benzenesulfonate

dimethyl (benzyloxy)((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methylphosphonate

methyl hydrogen (benzyloxy)((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methylphosphonate

dimethyl 2-(benzyloxy)-2-((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)ethylphosphonate