107692-06-8

Upstream product

• 2117-13-7 5-(trimethylsilyl)-4-pentyn-2-ol 
• 107692-04-6 (2R,3S)-(-)-3-benzyloxy-2-methylbutanal 
• 112996-11-9 (2S,3R)-(-)-3-benzyloxy-2-methylbutan-1-ol 
• 107692-05-7 (3S,4R)-(+)-4-benzyloxy-1,1-dibromo-2-methylpent-1-ene 
• 2117-11-5 4-pentyn-2-ol 
• 100-39-0 benzyl bromide 
• 119312-07-1 (2RS,3SR)-3-methyl-5-(trimethylsilyl)pent-4-yn-2-ol 
• 107692-02-4 (2R,3R)-2-methyl-1-(tetrahydropyran-2-yloxy)butan-2-ol 
• 107692-03-5 (2R,3R)-2-methyl-1-(tetrahydropyran-2-yloxy)butan-2-ol benzyl ether 

Downstream Products

• 107692-10-4 (2R,2'R,3'S,6'S,8'R,10'R)-2,4-dimethyl-(10'-diphenyl-t-butylsiloxy-2',3'-dimethyl-1',7'-dioxaspiro<5.5>undecan-8-yl)-hex-4-enoyl 4S-(propan-2-yl)oxazolidin-2-one 
• 113016-73-2 (2R,2'R,3'S,6'S,8'R,10'R)-(+)-6-(10'-diphenyl-t-butylsiloxy-2',3'-dimethyl-1',7'-dioxaspiro<5.5>undecan-8'-yl)-2,4-dimethylhex-4-enyl toluene-p-sulphonate 
• 101212-45-7 (2R,3S,6S,10R)-(E)-(+)-10-diphenyl-t-butylsiloxy-8<(5'R)-3',5'-dimethyl-6'-phenylsulphonylhex-2'-enyl>-2,3-dimethyl-1,7-dioxaspiro<5.5>undecan 
• 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 
• 101212-44-6 (2R,3S,6S,10R)-(E)-(+)-10-diphenyl-t-butylsiloxy-8<(5'R)-3',5'-dimethyl-6'thiophenylhex-2'-enyl>-2,3-dimethyl-1,7-dioxaspiro<5.5>undecan 
• 112995-99-0 Methanesulfonic acid (E)-4-[(2R,4S,6R,8R,9S)-4-(tert-butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-2-methyl-but-2-enyl ester 
• 107692-07-9 (2'R,3'S,6'S,8'S,10'R)-(E)-(+)-ethyl 4-(10'diphenyl-t-butylsiloxy-2',3'-dimethyl-1',7'-dioxaspiro<5.5>undecane-8'-yl)-2-methylbut-2-enoate 
• 112320-69-1 (2R,2'R,3'S,6'S,8'R,10'R)-(+)-6-(10'-diphenyl-t-butylsiloxy-2',3'-dimethyl-1',7'-dioxaspiro<5.5>undecan-8'-yl)-2,4-dimethylhex-4-enol 
• 107692-08-0 (2'R,3'S,6'S,8'R,10'R)-(E)-(+)-4-(10'diphenyl-t-butylsiloxy-2',3'-dimethyl-1',7'-dioxaspiro<5.5>undecan-8'-yl)-2-methylbut-2-enol 
• 107692-09-1 (2R,3S,6S,8S,10R)-(E)-10-diphenyl-t-butylsiloxy-2,3-dimethyl-8-(4'-iodo-3'-methylbut-2'enyl)-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 
• 119312-09-3 (3S,5S,10S,11R)-11-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-10-methyl-7-oxo-dodec-8-ynoic acid methyl ester 

Relevant academic research and scientific papers

Palladium- and copper-catalyzed 1,4-additions of organozinc compounds to conjugated aldehydes

Conjugated aldehydes undergo smooth Pd(OAc)2·PPh 3- or Me2CuCNLi2-catalyzed 1,4-addition of dialkylzinc reagents.

NEW STRATEGY IN THE STEREOCONTROLLED SYNTHESIS OF THE SPIRO KETAL SUBUNIT OF MILBEMYCINS

A double Baeyer-Villiger oxidation of bicyclo heptane-2,5-dione and a stereocontrolled alkylation of the dianion derived from 4-pentyn-2-ol are the salient features of a new strategy in the stereocontrolled synthesis of the spiroketal moiety of milbemycins.

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.

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