179548-99-3

Basic information

• Product Name: (Z)-1,4-bis((4-methoxybenzyl)oxy)but-2-ene
• Synonyms: (Z)-1,4-bis((4-methoxybenzyl)oxy)but-2-ene
• CAS NO: 179548-99-3
• Molecular Weight: 328.408
• Mol File: 179548-99-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (Z)-1,4-bis((4-methoxybenzyl)oxy)but-2-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-1,4-bis((4-methoxybenzyl)oxy)but-2-ene(179548-99-3)
• EPA Substance Registry System: (Z)-1,4-bis((4-methoxybenzyl)oxy)but-2-ene(179548-99-3)

Safety Data

• Hazardous Substances Data: 179548-99-3(Hazardous Substances Data)

Upstream product

• 6117-80-2 1,4-butenediol 
• 105-13-5 4-Methoxybenzyl alcohol 
• 2746-25-0 p-Methoxybenzyl bromide 
• 824-94-2 p-methoxybenzyl chloride 

Downstream Products

• 121289-23-4 p-methoxybenzyloxyacetaldehyde 
• 916604-37-0 (1S,3R,4S,5E)-4-hydroxy-7-[(4-methoxybenzyl)oxy]-1,3,5-trimethyl-2-oxohept-5-en-1-yl benzoate 
• 916604-67-6 (2R,4S,5R,E)-5-hydroxy-8-(4-methoxybenzyloxy)-4,6-dimethyl-3-oxooct-6-en-2-yl benzoate 
• 197227-70-6 (2E)-4-[(4-methoxybenzyl)oxy]-2-methylbut-2-enal 
• 181295-61-4 (2S,3R)-1-(4-Methoxy-benzyloxy)-3-methyl-pent-4-en-2-ol 
• 690634-42-5 C₂₂H₂₈O₄ 
• 690634-31-2 (2S,3R,4S)-4,5-Bis-(4-methoxy-benzyloxy)-3-methyl-pentane-1,2-diol 
• 690634-43-6 (2S,3R,4R)-1,2-Bis-(4-methoxy-benzyloxy)-3-methyl-9-trimethylsilanyl-nona-6,8-diyn-4-ol 
• 690634-32-3 (E)-(2S,3R,4R)-1,2-Bis-(4-methoxy-benzyloxy)-3-methyl-9-trimethylsilanyl-non-6-en-8-yn-4-ol 
• 1313191-18-2 (2S,3S)-1-(4-methoxybenzyloxy)-3-(methoxymethoxy)pent-4-en-2-ol 
• 1313191-19-3 ethyl 3-((4S,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propanoate 

Relevant articles and documents

Synthesis of a dihydropyranonucleoside using an oxidative glycosylation reaction mediated by hypervalent iodine

As a part of our ongoing studies of structure-activity relationships regarding cyclohexenyl nucleosides, we were prompted to synthesize a dihydropyranonucleoside as a potential anti-HIV agent. The synthesis of a glycal moiety started from but-2-enediol, which was converted into a di-PMB derivative in several steps. The introduction of an allyl group followed by ring-closing metathesis gave a dihydropyran derivative. After isomerization of the double bond catalyzed by Wilkinson's catalyst, the resulting glycal, 2,3-bis[(4-methoxybenzyloxy)methyl]-3,4-dihydro-2H-pyran, was subjected to an oxidative glycosylation reaction mediated by hypervalent iodine. Treatment of 2,3-bis[(4-methoxybenzyloxy)methyl]-3,4-dihydro-2H-pyran with (PhSe) 2/PhI(OAc)2/TMSOTf (cat.) gave the desired pyranyluracils as a mixture of anomers that were converted into the final target, dihydropyranocytidine, after several manipulations and separation of the anomers. Georg Thieme Verlag Stuttgart. New York.

Stereoselective synthesis of the C13-C28 subunit of (-)-laulimalide utilizing an α-chlorosulfide intermediate

A stereoselective route to the C13-C28 subunit of (-)-laulimalide is described. l-Tartaric acid is the source of the hydroxy groups at C19 and C20. An α-chlorosulfide is employed as the key intermediate for the creation of the C17-C18 bond and the C16-C17 double bond was introduced using the Mislow-Braverman rearrangement and Hutchin's dexoxygenation with concomitant double bond transposition reaction. The C15 and C23 stereogenic centers were created using catalytic asymmetric reactions. The trisubstituted and trans-disubstituted alkenes were created stereoselectively by taking advantage of ring-closing metathesis and the Julia-Kocienski olefination reaction, respectively. Georg Thieme Verlag Stuttgart, New York.

Stereoselective total synthesis of (+)-sapinofuranone B

Two approaches for the total synthesis of (+)-sapinofuranone B have been described. The first strategy utilizes the methodology developed earlier in our group to get the chiral propargyl alcohol and the second strategy involves generation of threo-1,2-diol derivative by diastereoselective and enantioselective addition of [(Z)-γ-methoxymethoxyallyl] diisopinocampheylborane onto aldehyde and cross metathesis as the key steps.