444308-38-7

Upstream product

• 923986-95-2 (1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1,2-diphenyl-1-hydroxy-ethyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.^9,11.0^2,17.0^8,13]-docosane 
• 923986-97-4 (1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1-phenyl-1-hydroxy-2-propenyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.^9,11.0^2,17.0^8,13]-docosane 
• 923986-89-4 (1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1-phenyl-1-hydroxy-ethyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.^9,11.0^2,17.0^8,13]-docosane 
• 636599-79-6 (1S,2R,5R,7S,9R)-5-[(1'S)-1'-hydroxy-1',3'-diphenyl-2'-propyn-1'-yl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane 
• 636599-75-2 (1S,2R,5R,7S,9R)-5-[(1'S)-1'-hydroxy-2'-methyl-1'-phenylpropyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane 
• 636599-78-5 (1S,2R,5R,7S,9R)-5-[(1'S)-1'-hydroxy-1'-phenyl-2'-propen-1'-yl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane 
• 636599-74-1 (1S,2R,5R,7S,9R)-5-[(1'S)-1'-hydroxy-1'-phenylpropyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane 
• 599192-60-6 (1S,2R,5R,7S,9R)-5-[(1'S)-1'-hydroxy-1'-phenylethyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane 
• 599192-58-2 (1S,2R,5R,7S,9R)-5-[(S)-(hydroxy)(phenyl)methyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane 
• 444308-45-6 (1S,2R,5R,7S)-5-[(R)-2'-hydroxy-1'-phenyl-2'-propyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane 
• 444308-42-3 (1S,2R,5R,7S)-5-[(R)-1'-hydroxy-1'-phenyl-1'-ethyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane 

Downstream Products

• 682352-08-5 (1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-hydroxymethyl-bicyclo[3.1.1]heptane 
• 682352-09-6 (1S,2R,3S,5R,2'R)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-hydroxymethyl-bicyclo[3.1.1]heptane 
• 923986-88-3 2,2-bis[(1S,2R,3S,5R)-2-hydroxymethyl-6,6-dimethylbicyclo[3.1.1]hept-3-ylsulfanyl]-1-phenylethanone 
• 923986-87-2 (1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-benzoyl-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.^9,11.0^2,17.0^8,13]-docosane 
• 923986-89-4 (1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1-phenyl-1-hydroxy-ethyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.^9,11.0^2,17.0^8,13]-docosane 
• 923986-97-4 (1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1-phenyl-1-hydroxy-2-propenyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.^9,11.0^2,17.0^8,13]-docosane 
• 923986-95-2 (1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1,2-diphenyl-1-hydroxy-ethyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.^9,11.0^2,17.0^8,13]-docosane 
• 923986-93-0 2,2-bis[(1S,2R,3S,5R)-2-(tert-butyl-dimethylsilanyloxymethyl)-6,6-dimethylbicyclo[3.1.1]hept-3-ylsulfanyl]-1-phenylethanone 
• 858658-57-8 (1S,2R,5R,7S,9R,1'R)-5-(1'-hydroxy-1'-phenyl-1'-propyl)-10,10-dimethyl-4-oxa-6-thia-tricyclo[7.1.1.0^2,7]undecane 
• 682352-10-9 (1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 
• 682352-11-0 (1S,2R,3S,5R,2'R)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 
• 682352-12-1 (1S,2R,3S,5R,1'S,2'R)-6,6-dimethyl-3-(1'-ethoxy-2'-phenyl-2'-hydroxy-1'-propylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 
• 682352-19-8 (1S,2R,3S,5R,1'R,2'S)-6,6-dimethyl-3-(1'-ethoxy-2'-phenyl-2'-hydroxy-1'-propylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 
• 682352-13-2 (1S,2R,3S,5R,1'S,2'R)-6,6-dimethyl-3-(1'-ethoxy-2'-phenyl-2'-hydroxy-1'-butylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 

Relevant academic research and scientific papers

Synthesis of a new (1R)-(-)-myrtenal-derived dioxadithiadodecacycle and its use as an efficient chiral auxiliary

(Chemical Equation Presented) The new macrocycle 9 (>70% yield from hydroxythiol 10) was treated with several nucleophilic reagents (RMgX, RLi, and LiAlH4) affording carbinols 12a-j (80-96% yield, >99:1 dr). Oxidative hydrolysis of 12a,c,e, followed by LiAlH4 reduction of the resulting mixture, gave 16a,c,e in >95% ee,16c being a key precursor for the preparation of fungicide 17. The absolute configuration of 9 and 12j (Nu = H) was established by single-crystal X-ray diffraction analyses and chemical correlation.

Enantioselective synthesis of 1-alkyl-substituted 1-phenyl-1,2-ethanediols using a myrtenal-derived chiral auxiliary

The enantioselective synthesis of several 1-phenyl-1,2-ethanodiol derivatives using 2-benzoyl-1,3-oxathiane 1 as a chiral auxiliary is described. Nucleophilic additions of Grignard reagents, methyl lithium and LS-Selectride on benzoyloxathiane 1 proceeded in >95% diastereomeric ratio (dr) affording the corresponding tertiary carbinols, which were successively hydrolyzed and reduced to give the title derivatives in >95% enantiomeric excess (ee).

Highly diastereoselective nucleophilic additions using a novel myrtenal-derived oxathiane as a chiral auxiliary

The synthesis of novel oxathiane 3 and its acetyl derivative 12, from commercially available (-)-myrtenal 4, is described. The addition of several nucleophilic reagents to 12 furnished the corresponding tertiary carbinols in highly diastereomeric excess. The hydrolysis of 11a, b yielded the expected α-hydroxycarbonyl compounds in excellent enantiomeric excess.