162630-99-1

Upstream product

• 100-39-0 benzyl bromide 
• 113321-58-7 (2S,3S)-diethyl 2,3-bis(phenylmethoxy)succinate 
• 171964-40-2 diisopropyl (2S,3S)-2,3-dibenzyloxysuccinate 
• 113350-84-8 (2R,3R)-(-)-2,3-bis(phenylmethoxy)-1,4-butanediol 
• 171622-74-5 (2R,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butan-1-ol 

Downstream Products

• 171863-58-4 (3R,4R)-3,4-dibenzyloxy-1,1-dibromo-5-tert-butyldimethylsilyloxypent-1-ene 
• 1359717-90-0 rac-(2R,3R)-2,3-bis(benzyloxy)pent-4-yn-1-ol 
• 1359717-86-4 (2S,3R)-2,3-bis(benzyloxy)pent-4-ynal 
• 1359717-93-3 (2R,3R,4R)-3,4-bis(O-benzyl)-1,1-difluoro-1-(phenylselanyl)-hex-5-yn-2,3,4-triol 
• 1359717-96-6 (2R,3S,4R)-2-acetoxy-3,4-bis(benzyloxy)-1,1-difluoro-1-phenylselanyl-hex-5-yne 
• 1359717-98-8 (4S,5R)-5-(O-acetyl)-4-(O-benzyl)-1,1-difluoro-2-methylcyclopent-2-en-4,5-diol 
• 171863-59-5 (((2R,3R)-2,3-bis(benzyloxy)pent-4-yn-1-yl)oxy)(tert-butyl)dimethylsilane 
• 171863-60-8 (5R,6R)-5,6-dibenzyloxy-6-tert-butyldimethylsilyloxy-2-methylhept-3-yn-2-ol 
• 197219-79-7 [(2S,3S,4R)-3,4-Bis-benzyloxy-2-((Z)-styryl)-tetrahydro-furan-2-yl]-thioacetic acid S-tert-butyl ester 
• 197219-80-0 (3S,4S,5R)-4,5-Bis-benzyloxy-3,6-dihydroxy-3-((Z)-styryl)-hexanethioic acid S-tert-butyl ester 
• 189328-23-2 ((2R,3S,4R)-3,4-Bis-benzyloxy-2-phenylethynyl-tetrahydro-furan-2-yl)-thioacetic acid S-tert-butyl ester 
• 197219-78-6 ((2S,3S,4R)-3,4-Bis-benzyloxy-2-phenylethynyl-tetrahydro-furan-2-yl)-thioacetic acid S-tert-butyl ester 
• 189328-22-1 (3S,4S,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-phenylethynyl-hexanethioic acid S-tert-butyl ester 
• 197219-77-5 (3S,4S,5R)-4,5-Bis-benzyloxy-3,6-dihydroxy-3-phenylethynyl-hexanethioic acid S-tert-butyl ester 

Relevant academic research and scientific papers

Correction to: Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H (Organic Letters (2016) 18: 15 (3886-3889) DOI: 10.1021/acs.orglett.6b

The wrong enantiomers of (?)-gabosine H (5), (?)-epigabosine H (epi-5) and intermediates 6?10, 11a,b, and 12?22 were drawn in the Abstract, Table of Contents, and Schemes 2?6. The correct structural drawings for these compounds are provided. The corrected

Synthesis of exo-methylenedifluorocyclopentanes as precursors of fluorinated carbasugars by 5-exo-dig radical cyclization

The synthesis of polyhydroxylated 1,1-difluoro-5-methylenecyclopentanes is described. The sequence involves an addition of PhSeCF2TMS to a tartrate-derived aldehyde or its corresponding tert-butanesulfinylimines followed by a radical cyclization. The use of a benzyl protected substrate led to an unproductive 1,5-hydrogen transfer after cyclization but the desired compound was eventually obtained from the unprotected substrate. A hydroboration/oxidation sequence was investigated on these 1,1-difluoro-5- methylenecyclopentanes as it would provide fluorinated carbasugars, a new and promising class of glycomimetics. Unfortunately, this reaction was poorly efficient and its regioselectivity not the expected one.

Enantio- and diastereoselective synthesis of cyclic β-hydroxy allylsilanes via sequential aldehyde γ-silylallylboration and ring-closing metathesis reactions

(Matrix presented) Highly enantioenriched cyclic allylsilanes are prepared via stereoselective γ-silylallylboration reactions of β- or γ-unsaturated aldehydes followed by ring-closing metathesis.

Total Syntheses of (+)-Secosyrins 1 and 2 and (+)-Syributins 1 and 2

First total syntheses of (+)-secosyrins 1 and 2 and total syntheses of (+)-syributins 1 and 2 are described. The two chiral centers of diisopropyl tartrate were incorporated into target natural products. Stereoselective construction of the spiro skeleton of secosyrins could be realized by taking advantage of an alkyne-cobalt complex. The synthesis of these compounds established their relative and absolute stereochemistry unambiguously.

Highly stereocontrolled total synthesis of (+)-bengamide E

Diisopropyl D-tartrate 7 was efficiently transformed into the hexacarbonyl dicobalt complexed aldehyde 23.A highly stereocontrolled aldol reaction of 23 with the O,S-acetal 20 in the presence of tin(IV) chloride provided, after decomplexation, the aldol adduct 21 as the sole product, which was subsequently converted into (+)-bengamide E 5.