107692-03-5

Upstream product

• 100-39-0 benzyl bromide 
• 107692-02-4 (2R,3R)-2-methyl-1-(tetrahydropyran-2-yloxy)butan-2-ol 
• 110-87-2 3,4-dihydro-2H-pyran 
• 88728-99-8 (R)-3-(tetrahydro-2-pyranyloxy)-2-methyl-1-propanol 
• 107869-51-2 (2S)-2-methyl-3-(tetrahydro-2H-pyran-2-yloxy)propanal 
• 88557-53-3 methyl 2(S)-methyl-3-tetrahydropyranyloxypropanoate 

Downstream Products

• 112996-11-9 (2S,3R)-(-)-3-benzyloxy-2-methylbutan-1-ol 
• 107865-54-3 (2R,3S,6S,8S,10S)-(+)-10-diphenyl-t-butylsilyloxy-2,3-dimethyl-8-(p-tolylsulphonyloxy)methyl-1,7-dioxaspiro<5.5>undecane 
• 107692-12-6 (2R,3S,6S,8R,10R)-(+)-10-diphenyl-t-butylsilyloxy-8-cyanomethyl-2,3-dimethyl-1,7-dioxaspiro<5.5>undecane 
• 104705-91-1 [(2S,4S,6R,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-acetaldehyde 
• 107692-11-5 (2R,3S,6S,8S,10S)-(+)-2,3-dimethyl-10-hydroxy-8-(p-tolylsulphonyloxy)methyl-1,7-dioxaspiro<5.5>undecane 
• 107692-06-8 (3S,4R)-4-benzyloxy-3-methylpent-1-yne 
• 107692-05-7 (3S,4R)-(+)-4-benzyloxy-1,1-dibromo-2-methylpent-1-ene 
• 107692-04-6 (2R,3S)-(-)-3-benzyloxy-2-methylbutanal 

Relevant academic research and scientific papers

A FORMAL SYNTHESIS OF (+)MILBEMYCIN β3: A WITTIG APPROACH

A new route has been established to generate the C14-C15 trisubstituted double bond of milbemycin β3 by reaction of a Wittig reagent with the appropriate spiroacetal aldehyde.The product of this reaction, after conversion to the iodide and enan

Preparation of a Chiral Lactone from Leavoglucosan; a Key Intermediate for Synthesis of the Spiroacetal Moietes of the Avermectins and Milbemycins

A synthesis of two diprotected (4S,6S)-4-hydroxy-6-hudroxymethyltetrahydropyran-2-ones has been developed from laevoglucosan.Reaction of these lactones with a substituted chiral lithium acetylide followed by hydrogenation and acid-catalysed cyclisation led to formation of the spiroacetal moiety of milbemycin α1 and α3.The acetylene was prepared by resolution of racemic material obtained from reaction of lithium acetylide and cis-butene epoxide.Alternatively a stereocontrolled synthesis was developed from (S)-methyl-3-hydroxy-2-methylpropionate which involved 'chelation controlled' addition of lithium dimethylcuprate to the corresponding tetrahydropyranyloxy aldehyde.