118427-95-5

Upstream product

• 150919-18-9 (2Z,4E)-1-tetrahydropyranyloxy-6-tert-butyldiphenylsilyloxy-2,4-hexadiene 
• 150919-17-8 (2E,4Z)-ethyl 6-tetrahydropyranyloxy-2,4-hexadienoate 
• 145262-24-4 (2E,4Z)-6-tetrahydropyranyloxy-2,4-hexadien-1-ol 
• 150919-19-0 (2Z,4E)-6-([tert-butyl(diphenyl)silyl]oxy)-hexa-2,4-dien-1-ol 
• 77774-01-7 (1R,4S)-(4-hydroxymethylcyclobut-2-enyl)methanol 
• 10374-07-9 cyclobut-3-ene-1,2-dicarboxylic acid anhydride 
• 154613-57-7 6-(t-butyldiphenylsilyloxy)-(2Z,4E)-hexadienal 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 154613-58-8 1-(t-butyldiphenylsilyloxy)hepta-(2E,4Z)-diene 
• 141935-67-3 (2Z,8Z,10E)-12-tert-butyldiphenylsiloxy-1-chloro-2-methoxy-6,6-bis(methoxycarbonyl)-3-methyldodeca-2,8,10-triene 
• 141935-66-2 (2Z,8Z,10E)-12-tert-butyldiphenylsiloxy-2-methoxy-6,6-bis(methoxycarbonyl)-3-methyldodeca-2,8,10-trien-1-ol 
• 141935-68-4 (3Z,9Z,11E)-13-tert-butyldiphenylsiloxy-3-methoxy-1,1,7,7-tetrakis(methoxycarbonyl)-4-methyltrideca-3,9,11-triene 
• 118427-96-6 2-[(2Z,4E)-6-(tert-Butyl-diphenyl-silanyloxy)-hexa-2,4-dienyl]-2-((Z)-6-methanesulfonyloxy-3-methyl-hex-3-enyl)-malonic acid dimethyl ester 
• 118427-86-4 2-[(2Z,4E)-6-(tert-Butyl-diphenyl-silanyloxy)-hexa-2,4-dienyl]-2-((Z)-6-hydroxy-3-methyl-hex-3-enyl)-malonic acid dimethyl ester 
• 118436-64-9 (5E,11Z,13E)-15-(tert-Butyl-diphenyl-silanyloxy)-2,9,9-tris-methoxycarbonyl-6-methyl-pentadeca-5,11,13-trienoic acid methyl ester 
• 118427-87-5 (5Z,11Z,13E)-15-(tert-Butyl-diphenyl-silanyloxy)-2,9,9-tris-methoxycarbonyl-6-methyl-pentadeca-5,11,13-trienoic acid methyl ester 
• 70979-88-3 (2E,4Z)-hepta-2,4-dien-1-ol 
• 33580-05-1 1,3-trans,5-cis-octatriene 
• 141935-65-1 (2Z,8Z,10E)-1-benzoyloxy-12-tert-butyldiphenylsiloxy-2-methoxy-6,6-bis(methoxycarbonyl)-3-methyldodeca-2,8,10-triene 
• 122598-95-2 (3Z,9Z,11E)-5-benzyloxy-13-<(tert-butyldiphenylsilyl)oxy>-1-methanesulfonyloxy-7,7-dimethoxycarbonyl-3-methyltrideca-3,9,11-triene 
• 118436-63-8 2-[(Z)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-hex-3-enyl]-2-[(2Z,4E)-6-(tert-butyl-diphenyl-silanyloxy)-hexa-2,4-dienyl]-malonic acid dimethyl ester 
• 118427-88-6 (5E,11Z,13E)-15-(tert-Butyl-diphenyl-silanyloxy)-9,9-bis-methoxycarbonyl-6-methyl-pentadeca-5,11,13-trienoic acid methyl ester 

Relevant academic research and scientific papers

Use of cis-3-cyclobutene-1,2-dimethanol in stereoselective routes to some naturally occurring conjugated dienes and trienes

Thermal electronic ring-opening of 4-alkyl-2-cyclobutene-1-carbaldehydes occurs at low temperature to give (2Z,4E)-alka-2,4-dienals exclusively, and this process is exploited en route to various isomeric naturally occurring 1,3,5-alkatrienes and 2,4-decadienoates from a single precursor, cis-3-cyclobutene-1,2-dimethanol 4.

The preparation and electrocyclic ring-opening of cyclobutenes: Stereocontrolled approaches to substituted conjugated dienes and trienes

Thermal electrocyclic ring-opening of 4-alkyl-2-cyclobutene-1-carbaldehydes occurs at low temperature to give (2Z,4E)-alkadienals exclusively, and the process is exploited in transforming cis-3-cyclobutene-1,2-dimethanol 1 into a variety of naturally occurring 1,3,5-alkatrienes and 2,4-decadienoates. Desymmetrisation of 1 with Pseudomonas fluorescens lipase gives access to both enantiomers of 3-oxabicyclo[3.2.0]hept-6-en-2-one 4, for use in stereocontrolled routes to 6-oxygenated (2Z,4E)-alkadienals.

Transannular Diels-Alder reactions on 14-membered macrocyclic trienes. Part I: stereoselective syntheses of the macrocyclic trienes precursors

Transannular Diels-Alder reactions on 14-membered macrocycles containing properly located diene and methyl-substituted dienophile units lead to A.B.C. tricycles related to steroids.To study the influence of the olefin and diene geometry on the stereochemical outcome of the Diels-Alder reaction it was necessary to prepare macrocyclic trienes of well-defined stereochemistry.Eight different types of macrocyclic trienes might be obtained by the coupling of appropriate dienophiles and dienes, namely, TTC, TTT, TCC, TCT, CTC, CTT, CCC, and CCT.In this paper (first in a series of two), the synthesis of appropriately functionalized dienophile and diene synthons, as well as their coupling reaction affording macrocyclic triene precursors, is described.

Synthesis and transannular Diels-Alder reaction of a 13-membered macrocyclic triene. A synthetic approach towards the tricyclic part A.B.C.[6.6.5] of the veratrum alkaloids

The syntheses of the acyclic triene cis-trans-trans (3Z,9Z,11E)-13-chloro-3-methoxy-1,1,7,7-tetrakis(methoxycarbonyl)-4- methyltrideca-3,9,11-triene (25), and the corresponding trans-cis-trans (3Z,9E,11E) isomer 37, and trans-trans-trans (3Z,9E,11E) isomer, 46, are described. Compounds 25 and 37 furnished in good yield 13-membered macrocyclic compounds (3Z,9Z,11E)- and (3Z,9E,11Z)-3-methoxy-1,1,7,7-tetrakis(methoxycarbonyl)-4- methylcyclotride-ca-3,9,11-triene (26) and (38) which led to tricyclic compound (cis-anti-cis)-2-methoxy-4,4,11,11-tetrakis(methoxycarbonyl)-1- methyl-tricyclo[7.4.0.02,6]tridec-7-ene (27) by transannular Diels-Alder reaction. Macrocyclization of trans-trans-trans chloride 46 was not successful.