175398-31-9

Upstream product

• 175398-30-8 (S)-2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopentanone 
• 243464-45-1 (S)-6-(tert-butyl-diphenylsilyloxy)-hexane-1,5-diol 
• 161561-86-0 (S)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-5,6-dihydro-2H-pyran-2-one 
• 913636-40-5 (S)-dihydropyranylmethoxy(tert-butyl)diphenylsilane 
• 51450-44-3 (2S)-(tetrahydro-2H-pyran-2-yl)methanol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 243464-44-0 (2S)-6-benzyloxy-1-(tert-butyldiphenylsilyloxy)-hex-4-yn-2-ol 
• 106731-74-2 tert-butyl[(2S)-oxiran-2-ylmethoxy]diphenylsilane 

Downstream Products

• 328534-76-5 (2S,10S,11R)-1-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-12-(4-methoxy-benzyloxy)-11-methyl-10-trimethylsilanyloxy-dodec-7-yn-6-one 
• 959982-59-3 10-(tert-butyl-diphenyl-silanyloxy)-9-hydroxy-dec-1-en-5-one 
• 1430851-97-0 [(2S',6S',8S')-8-{[(tert-butyldiphenylsilyl)oxy]methyl}-1',7'-dioxaspiro[5.5]undecan-2'-yl]methanol 
• 1392104-11-8 (3S,11S)-11-(tert-butyldimethylsilyloxy)-12-(tert-butyldiphenylsilyloxy)-7-(1,3-dioxolan-2-yl)dodec-1-yn-3-ol 
• 1392104-51-6 ((2S,6S,8S)-8-(1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl)-1,7-dioxaspiro[5.5]undecan-2-yl)methanol 
• 1392104-50-5 ((2S,6S,8S)-8-(1-(3-methoxyphenyl)-1H-1,2,3-triazol-4-yl)-1,7-dioxaspiro[5.5]undecan-2-yl)methanol 
• 1392104-47-0 1-(4-(4-((2S,6S,8S)-8-(hydroxymethyl)-1,7-dioxaspiro[5.5]undecan-2-yl)-1H-1,2,3-triazol-1-yl)phenyl)ethanone 
• 1392104-49-2 4-((2S,6S,8S)-8-((tert-butyldiphenylsilyloxy)methyl)-1,7-dioxaspiro[5.5]undecan-2-yl)-1-(3-nitrophenyl)-1H-1,2,3-triazole 
• 1392104-10-7 (9S)-9-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-5-(1,3-dioxolan-2-yl)decanal 
• 1392104-48-1 4-((2S,6S,8S)-8-((tert-butyldiphenylsilyloxy)methyl)-1,7-dioxaspiro[5.5]undecan-2-yl)-1-(3-methoxyphenyl)-1H-1,2,3-triazole 
• 1392104-41-4 1-(4-(4-((2S,6S,8S)-8-((tert-butyldiphenylsilyloxy)methyl)-1,7-dioxaspiro[5.5]undecan-2-yl)-1H-1,2,3-triazol-1-yl)phenyl)ethanone 
• 1392104-40-3 methyl 6-(4-((2S,6S,8S)-8-((tert-butyldiphenylsilyloxy)methyl)-1,7-dioxaspiro[5.5]undecan-2-yl)-1H-1,2,3-triazol-1-yl)hexanoate 
• 1392104-39-0 1-(10-(tert-butyldimethylsilyloxy)decyl)-4-((2S,6S,8S)-8-((tert-butyldiphenylsilyloxy)methyl)-1,7-dioxaspiro[5.5]undecan-2-yl)-1H-1,2,3-triazole 
• 1392104-38-9 11-(4-(8-((tert-butyldiphenylsilyloxy)methyl)-1,7-dioxaspiro[5.5]undecan-2-yl)-1H-1,2,3-triazol-1-yl)undecan-2-one 

Relevant academic research and scientific papers

Highly chemoselective oxidation of 1,5-diols to δ-lactones with TEMPO/BAIB

The selective oxidative conversion of a variety of highly functionalized 1°,2°-1,5-diols into the corresponding δ-lactones has been effected simply and efficiently using a reagent system comprised of catalytic 2,2,6,6-tetramethylpiperidinooxy (TEMPO) and

A concise and efficient synthesis of spiroketals - Application to the synthesis of SPIKET-P and a spiroketal from bactrocera species

We report the synthesis of spiroketals by sequence of enol ether synthesis and cyclization. The enol ethers were prepared from lactones by a Julia olefination reaction, and the starting chiral lactone was prepared from an industrial intermediate. This route is a concise and efficient way to synthesize naturally occurring and biologically interesting spiroketals. We used this sequence for the preparation of SPIKET-P and a spiroketal from Bactrocera species. Copyright

Direct kinetic formation of nonanomeric [6.5]-spiroketals in aqueous media

(Chemical Equation Presented) The direct kinetic formation of spiroketals from mixed ketal-alcohol precursors under acid catalysis was studied using four differently substituted systems. In all cases, the exclusive formation of the anomeric isomer was obs

Expedient access to the okadaic acid architecture: A novel synthesis of the C1-C27 domain

A newly designed synthetic entry to the C1-C27 domain of okadaic acid has been developed. This incorporates substantial improvements in the preparations of the key okadaic acid building blocks representing the C3-C8, C9-C14, and C16-C27 portions. The synthesis of the C3-C8 lactone used (R)-glycidol as the origin of the C4 stereogenic center and featured a late-stage optional incorporation of the C7 hydroxyl group. The complementary C9-C14 fragment was synthesized in a concise route from (R)-3-tert-butyldimethylsilyloxy-2-methylpropanal and propargyl bromide. Assembly of the C3-C14 spiroketal-containing intermediate from the constituent fragments revealed a dramatic effect of C7 functionalization upon spiroketalization efficiency. In contrast, both (9E)- and (9Z)-enones converged readily to the C8 spiroketal upon treatment with acid. Modifications to the central C16-C27 fragment of okadaic acid included the early replacement of benzylic protecting groups by more suitable functionalities to facilitate both the generation of the C15-C27 intermediate and the deprotection of the final products. These modular building blocks were deployed for the synthesis of the C1-C27 scaffold of 7-deoxyokadaic acid. This work demonstrates improvements in the formation of versatile okadaic acid intermediates, as well as a reordering of fragment couplings. This alternative order of coupling was designed to promote the late stage incorporation of nonnatural lipophilic extensions from the C27 terminus.

Abbreviated synthesis of the C3-C14 (substituted 1,7-dioxaspiro[5.5]undec-3-ene) system of okadaic acid.

[formula: see text] Described is a novel, concise, and flexible synthesis of the C3-C14 portion of okadaic acid. A substituted valerolactone (C3-C8) was prepared in three steps and alpha-hydroxylated using Davis' oxaziridine. Conjugate addition of dimethy

Total synthesis of the marine natural product 7-deoxy-okadaic acid: A potent inhibitor of serine/threonine-specific protein phosphatases

A small change to the structure of okadaic acid (1), the omission of the single hydroxy group at C7, facilitated substantially the first total synthesis of the derivative 7-deoxyokadaic acid (2). The conformation of 2 is in agreement with that of 1 and th

A chemoenzymatic preparation of both enantiomers of ω-hydroxymethyl-substituted lactones

(R)- and (S)-δ-hydroxymethyl valerolactone and ε-hydroxymethyl caprolactone were prepared as tert-butyldiphenylsilyl derivatives, in good yield and high enantiomeric purities, in a 5 step sequence, starting from the microbial stereospecific reduction of ethyl 2-oxocyclopentane or 2-oxocyclohexane carboxylates respectively.