113002-29-2

Upstream product

• 4728-12-5 2,2-dimethyl-5-hydroxymethyl-1,3-dioxane 
• 5056-07-5 (S)-methyl p-tolyl sulfoxide 
• 77-76-9 2,2-dimethoxy-propane 
• 82962-54-7 2,2-dimethyl-5-ethoxycarbonyl-1,3-dioxane 
• 133384-73-3 5-(toluenesulfonyloxymethyl)-2,2-dimethyl-1,3-dioxane 
• 1519-39-7 (R)-methyl p-tolyl sulfoxide 
• 51335-75-2 2,2-Dimethyl-1,3-dioxacyclohexane-5,5-dicarboxylic acid,diethyl ester 
• 97827-17-3 5-iodomethyl-2,2-dimethyl-1,3-dioxane 
• 66536-78-5 (+)-(R)-1-(p-tolylsulfinyl)-2-propanone 

Downstream Products

• 113002-31-6 (3S)-(R_S)-3-benzyloxymethyl-3,4-dihydro-6-methyl-5-p-tolylsulfinyl-2H-pyran 
• 113002-27-0 [(R)-6-Methyl-5-((R)-toluene-4-sulfinyl)-3,4-dihydro-2H-pyran-3-yl]-methanol 
• 113002-27-0 [(S)-6-Methyl-5-((S)-toluene-4-sulfinyl)-3,4-dihydro-2H-pyran-3-yl]-methanol 
• 113002-35-0 [(R)-6-Methyl-5-((S)-toluene-4-sulfinyl)-3,4-dihydro-2H-pyran-3-yl]-methanol 
• 113002-30-5 (S)-1-Methyl-7-((S)-toluene-4-sulfinyl)-2,6-dioxa-bicyclo[2.2.2]octane 
• 113002-30-5 (R)-1-Methyl-7-((S)-toluene-4-sulfinyl)-2,6-dioxa-bicyclo[2.2.2]octane 
• 113002-28-1 6-Hydroxy-5-hydroxymethyl-3-((R)-toluene-4-sulfinyl)-hexan-2-one 

Relevant academic research and scientific papers

Synthetic studies on spiroketal natural products. IV. A stereoselective synthesis of (3S,5S,6R,9R,R(S))-3-benzyloxymethyl-9-hydroxymethyl-5-(p-tolyl)sulfin yl-1,7-dioxaspiro[5.5]undecane, a key intermediate for talaromycins

A dioxaspiro compound (4), a common intermediate for the synthesis of talaromycin A (1) and (-)-talaromycin B (2), was synthesized by two routes utilizing two kinds of asymmetric recognition of prochiral 1,3-diols controlled by sulfinyl chirality, that is, firstly by acid promoted diastereoselective C-O bond fission of the bicyclic acetal (7) to give the dihydropyran derivative (6), which has an S-hydroxymethyl group at the C3-position (7 → 6), and secondly by diastereoselective intramolecular Michael addition of the diol (5), in which the three chiral centers at C5, C6, C9 were constructed in one step (5 → 4).

ASYMMETRIC FUNCTIONALIZATION AT A PROCHIRAL CARBON CENTER BY THE AID OF SULFINYL CHIRALITY: A SELECTIVE FORMATION OF 6-SUBSTITUTED (3R,SS)- AND (3S,SS)-3-HYDROXYMETHYL-3,4-DIHYDRO-5-(p-TOLYL)SULFINYL-2H-PYRANS

A successful asymmetric functionalization of prochiral gem-bis(hydroxymethyl) groups has been achieved by the aid of a sulfinyl chirality.