70326-39-5

Upstream product

• 70326-34-0 3-(2-benzyloxy-hexanoyl)-thiazolidine-2-thione 
• 96302-57-7 (1-Dimethoxymethyl-pentyloxymethyl)-benzene 
• 636-36-2 rac-2-hydroxyhexanoic acid 
• 4938-52-7 1-hepten-3-ol 
• 110-62-3 pentanal 
• 68756-64-9 2-hydroxyhexanoic acid methyl ester 
• 70326-41-9 2-benzyloxy-hexanoyl chloride 
• 70326-42-0 2-benzyloxy-hexanoic acid 
• 110320-68-8 methyl 2-benzyloxyhexanoate 
• 100-39-0 benzyl bromide 
• 119404-52-3 2-Benzyloxy-hexanoic acid benzyl ester 
• 141554-36-1 2-(benzyloxy)hexan-1-ol 
• 54620-75-6 (1-Vinyl-pentyloxymethyl)-benzene 
• 84994-58-1 (R)-1-((S)-2-Phenyl-hexahydro-pyrrolo[1,2-c]imidazol-3-yl)-pentan-1-ol 

Downstream Products

• 66832-04-0 methyl 6-benzyloxy-5-hydroxy-3-oxodecanoate 
• 106225-84-7 2-(1'-benzyloxypentyl)-2,3-dihydro-6-methoxypyran-4-one 
• 54620-78-9 6-<1-(Benzyloxy)hexyl>-5,6-dihydro-4-methoxy-2H-pyran-2-one 
• 66832-04-0 methyl 5-benzyloxy-6-hydroxy-8-oxodecanoate 
• 91751-29-0 (3R,4S,5S)-5-Benzyloxy-3-methyl-non-1-en-4-ol 
• 91751-29-0 (3S,4S,5S)-5-Benzyloxy-3-methyl-non-1-en-4-ol 
• 54620-78-9 6-(1'-benzyloxypentyl)-5,6-dihydro-4-methoxypyran-2-one 
• 54620-78-9 6-(1'-benzyloxypentyl)-5,6-dihydro-4-methoxypyran-2-one 
• 99035-38-8 [(4R,5R)-5-(1-Benzyloxy-pentyl)-2,4-dimethyl-4,5-dihydro-furan-3-yl]-tert-butyl-dimethyl-silane 
• 99035-38-8 [(4R,5S)-5-(1-Benzyloxy-pentyl)-2,4-dimethyl-4,5-dihydro-furan-3-yl]-tert-butyl-dimethyl-silane 
• 99052-84-3 [(R)-5-((R)-1-Benzyloxy-pentyl)-2-methyl-4,5-dihydro-furan-3-yl]-tert-butyl-dimethyl-silane 
• 87604-60-2 (S)-(+)-2-benzyloxyhexan-1-ol 
• 84994-64-9 (S)-2-O-benzyl hexane-1,2-diol 

Relevant academic research and scientific papers

Concentration effects in chelation controlled reactions

The diastereoselectivities of addition reactions of allyltrimethylsilane to an α-benzyloxyaldehyde were found to be relatively insensitive to the amount of added TiCl4, and to the absolute concentration of the 1:1 aldehyde/TiCl4 complex. In contrast, diastereoselectivities of similar additions to a structurally related β-benzyloxyaldehyde were highly dependent on these variables.

An aldol - Bislactonization route to α-methylene bis-γ-butyrolactones

The syntheses of α-methylene γ-butyrolactones and α-methylene bis- γ-butyrolactones are made simple through the use of the versatile dimethyl itaconate - anthracene adduct, 1.

High Diastereoselection in the Aldol Reaction of the Bistrimethylsilyl Enol Ether of Methyl Acetoacetate with 2-Benzyloxyhexanal: Synthesis of (-)-Pestalotin

Aldol condensation of the bistrimethylsilyl enol ether of methyl acetoacetate, compound 2, with 2-benzyloxyhexanal 3c affords highly selectively (99:1) the syn-aldol adduct 4c in the presence of titanium tetrachloride.The stereocontrolled synthesis of (-)-pestalotin 7 has been achieved.

Asymmetric Hetero-Diels-Alder Reaction of α-Alkoxy Aldehydes with Activated Dienes. The Scope of Lewis Acid Chelation-Controlled Cycloadditions

The cycloaddition reactions of various α-alkoxy aldehydes with 1,3-dimethoxy-1--1,3-butadiene (Brassard's diene, 2) were performed under the Lewis acid catalysis of Eu(hfc)3, magnesium dibromide, or diethylaluminum chloride.Moderate to high diastereoselectivities were observed with Eu(hfc)3 and magnesium dibromide.Evidence from reactions of Eu(hfc)3 and magnesium dibromide catalysis indicated a possible "chelation-control" pathway.Lewis acid catalysis from diethylaluminum chloride provides products with moderate to high diastereoselectivity.The mechanistic pathway with catalysis by diethylaluminum chloride was less clear.A possible mechanism based upon a "Cram" addition is considered.

AN ASYMMETRIC SYNTHESIS OF α-BENZYLOXY ALDEHYDES HAVING A CHIRAL TERTIARY CENTER - AN APPLICATION TO THE ASYMMETRIC SYNTHESIS OF exo-(+)-BREVICOMIN -

α-benzyloxy aldehydes having a chiral tertiary center at α-carbon atom are synthesized in high enantiomeric excess by successive treatment of 2-methoxycarbonyl-3-phenyl-1,3-diazabicyclooctane with diisobutylaluminum hydride (DIBAL-H) and Grignard reagents.The asymmetric reaction is applied to the total synthesis of exo-(+)-brevicomin.