366011-51-0

Basic information

• Product Name: (4S,5S)-4-((Z)-(R)-1-Benzyloxy-7-triisopropylsilanyl-hept-4-ene-2,6-diynyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolane
• Synonyms: (4S,5S)-4-((Z)-(R)-1-Benzyloxy-7-triisopropylsilanyl-hept-4-ene-2,6-diynyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolane
• CAS NO: 366011-51-0
• Molecular Weight: 596.998
• Mol File: 366011-51-0.mol

Chemical Properties

• CAS DataBase Reference: (4S,5S)-4-((Z)-(R)-1-Benzyloxy-7-triisopropylsilanyl-hept-4-ene-2,6-diynyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolane(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5S)-4-((Z)-(R)-1-Benzyloxy-7-triisopropylsilanyl-hept-4-ene-2,6-diynyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolane(366011-51-0)
• EPA Substance Registry System: (4S,5S)-4-((Z)-(R)-1-Benzyloxy-7-triisopropylsilanyl-hept-4-ene-2,6-diynyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolane(366011-51-0)

Safety Data

• Hazardous Substances Data: 366011-51-0(Hazardous Substances Data)

Upstream product

• 149776-81-8 (Z)-hex-3-en-1,5-diynyl-triisopropylsilane 
• 108817-97-6 (4R,5S)-5-tert-butyldimethylsilyloxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde 
• 100-39-0 benzyl bromide 
• 366011-43-0 (Z)-(R)-1-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-7-triisopropylsilanyl-hept-4-ene-2,6-diyn-1-ol 

Downstream Products

• 366011-45-2 [(4S,5S)-5-((Z)-(R)-1-Benzyloxy-7-iodo-hept-4-ene-2,6-diynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol 
• 366011-46-3 (4R,5S)-5-((Z)-(R)-1-Benzyloxy-7-iodo-hept-4-ene-2,6-diynyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 
• 366011-44-1 [(4S,5S)-5-((Z)-(R)-1-Benzyloxy-hept-4-ene-2,6-diynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol 

Relevant articles and documents

A mild route to α-alkoxyacetylenes mediated by Lewis acids and synthetic routes to 10-, 11-, and 12-membered ring enediyne carbocycles

The condensation of silyl substituted acetylenes with dimethoxy acetals via a modified "Mukaiyama-type reaction" to afford α-alkoxyacetylenes is described. These propargylic ethers 17-21 were synthesized from the reaction of aluminum or zinc acetylides with acetals mediated by Lewis acids. In appropriate cases, when a second acetal was present in the initial acyclic product (24), a subsequent intramolecular acetal-ene (Prins) cyclization ensued to afford the silylalkylidenealkoxycyclopentane (25). Enediyne species were unreactive under these conditions, even in an intramolecular case. Routes to 11-and 12-membered carbocyclic enediyne compounds (43, 44) were developed via an intramolecular pinacol coupling of the dialdehydes 39 with sammarium diodide/HMPA. The requisite double bond was introduced using the thiocarbonate expulsion method with trimethyl phosphite. A route to the highly substituted 10-membered ring enediyne 50 is also described based on the use of an isopropylidene acetal tether control group to facilitate an intramolecular chromium (II)/nickel (II)-mediated coupling of the iodoacetylene aldehyde 49.