38726-53-3

Upstream product

• 74524-10-0 (1R,6S,8R)-8-dodecyl-3,3-dimethyl-2,4-dioxa-7-azabicyclo<4.4.0>-decane 
• 153198-51-7 (2S,3R,6R)-3-benzyloxy-6-dodecyl-2-(methoxymethoxy)methylpiperidine 
• 336625-44-6 (2S,3R)-3-benzyloxy-2-benzyloxymethyl-6-dodecyl-2,3,4,5-tetrahydropyridine 
• 849428-89-3 (2S,3R,6S)-(3-benzyloxy-6-dodecylpiperidin-2-yl)methanol 
• 349556-00-9 (2S,3R)-1-(tert-butyldimethylsilanyloxy)-3-benzyloxy-2-dibenzylamino-6-oxooctadecan-6-one 
• 849428-94-0 (2S,3R,6R)-3-Benzyloxy-6-dodecyl-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester 
• 941715-59-9 (2S,3R,6R)-2-(acetoxymethyl)-6-dodecylpiperidin-3-yl acetate 
• 958020-53-6 tert-butyl (1S,2S,4R,6R)-6-dodecyl-2-phenylhexahydro[1,3]dioxino[5,4-b]pyridine-5-carboxylate 
• 849428-93-9 ((1S,2R)-2-Benzyloxy-1-hydroxymethyl-5-oxo-heptadecyl)-carbamic acid benzyl ester 
• 849428-92-8 [(1S,2R)-2-Benzyloxy-4-(2-dodecyl-[1,3]dioxolan-2-yl)-1-hydroxymethyl-butyl]-carbamic acid benzyl ester 
• 849428-90-6 (2S,3R)-3-benzyloxy-2-dibenzylamino[1,3]dioxolan-6-yl-octadecan-1-ol 
• 165601-77-4 2-tetradecenoic acid ethyl ester 
• 336625-39-9 tert-butyl (4S,1'R)-4-(1'-benzyloxy-4'-pentenyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 693-67-4 bromoundecane 

Relevant academic research and scientific papers

Stereoselective total syntheses of (-)-desoxoprosopinine and (-)-desoxoprosophylline: Palladium(0)-catalyzed intramolecular N-alkylation for the key piperidine ring formation

Intramolecular N-alkylation of D-glucose-derived substrate 21E proceeded in an S(N)2' mode smoothly in the presence of a Pd(0) catalyst and n-Bu4NI. The major cyclization product, a 2,6-dialkylated piperidine 22t, was effectively converted into the title alkaloids.

Stereoselective Syntheses of (+)-2- epi -Deoxoprosopinine, (-)-Deoxoprosophylline, (+)- cis -195A, and 2,5-Di- epi - Cis -195A from a Common Chiral Nonracemic Building Block

Approaches toward the syntheses of alkaloids belonging to the 2,6-disubstituted 3-hydroxypiperidine and cis-decahydroquinoline (cis-DHQ) classes of alkaloids are developed, starting from a common chiral nonracemic bicyclic lactam lactone (BLL). Two key δ-

A concise and divergent approach to hydroxylated piperidine alkaloids and Azasugar Lactams

The vinylogous Mannich reaction (VMR) between 2-(tertbutyldimethylsilyloxy) furan (TBSOF) and (RS)-t-BS-imine 12a and the application of the VMR adduct butenolide 13a as a versatile chiral building block for the synthesis of hydroxylated piperidine alkaloids and azasugars were investigated. Firstly, both the anti diastereoselectivity and the chemical yield of the asymmetric VMR between TBSOF and (RS)-t-BS-imine 12a were improved by the use of Sm(OTf)3/ H2O (1.5 equiv.) as the promoter. Similar diastereoselectivities were also obtained with Yb(OTf)3/H2O, Cu(OTf)2/H2O, Zn(OTf)2/H2O, or the Br?nsted acids TfOH or MsOH as the promotors. Secondly, an efficient four-step procedure for the elaboration of butenolide 13a into piperidine alkaloid (–)-deoxoprosophylline (2) was established. Thirdly, by taking advantage of the olefin functionality in the butenolide 13a, polyhydroxylated δ-lactams 23 and 21, which are ready precursors of azasugars L-deoxyallonojirimycin (ent-7) and L-3- epi-fagomine (ent-6), were obtained in two and three steps, respectively, via dihydroxylated lactone 17. The easily available synthetic intermediate 17 can also serve as a key intermediate for the synthesis of the glycosyl nucleoside amino acid cores of polyoxins and nikkomycins.

A concise total synthesis of (+)-deoxocassine and (-)-deoxoprosophylline from d-xylose

A concise total synthesis of (+)-deoxocassine (1) and (-)- deoxoprosophylline (2) has been achieved for the first time from d-xylose. The key steps involved in these synthesis are alkyl Grignard reaction, S N2 substitution of mesylate by azide,

Synthesis of (-)-deoxoprosophylline, (+)-2- epi -deoxoprosopinine, and (2 R,3 R)- and (2 R,3 S)-3-hydroxypipecolic acids from d -glycals

(Figure presented) New syntheses of (-)-deoxoprosophylline, (+)-2-epi-deoxoprosopinine, and (2R,3R)- and (2R,3S)-3-hydroxypipecolic acids are reported. Utilization of the chiral functionalities of Perlin aldehydes, derived from 3,4,6-tri-O-benzyl glycals,

Asymmetric synthesis of N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine, jaspine B (pachastrissamine), 2-epi-jaspine B, and deoxoprosophylline via lithium amide conjugate addition

The highly diastereoselective anti-aminohydroxylation of (E)-γ-tri-iso-propylsilyloxy-α,β-unsaturated esters, via conjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide and subsequent in situ enolate oxidation with (+)-(camphorsulfonyl)oxaziri

Concise asymmetric synthesis of (-)-deoxoprosophylline

An efficient asymmetric synthesis of the 2-hydroxymethyl 3,6-disubstituted piperidine alkaloid, (-)-deoxoprosophylline, is described. The key step of this route is the SmI2-mediated cross-coupling of chiral N-tert-butanesulfinyl imine 9 with al

Synthesis of enantioenriched 2- and 2,6-substituted piperidin-3-ols from α-dibenzylamino aldehydes

Homochiral α-dibenzylamino aldehydes react with 4-butenylmagnesium bromide in diethyl ether at 0°C to yield anti-β-amino alcohols in excellent yield and dr. These anti diastereoisomers were transformed into enantioenriched 2- and 2,6-substituted 3-piperid

Synthesis of two piperidine alkaloids, (-)-deoxoprosopinine and (-)-deoxoprosophylline, from 6-hydroxylated dihydrosphingosine derivatives

(-)-Deoxoprosopinine 1 [(2S,3R,6S)-6-dodecyl-2-hydroxymethylpiperidin-3-ol] and (-)-deoxoprosophylline 3 [(2S,3R,6R)-6-dodecyl-2-hydroxymethylpiperidin-3-ol] were synthesized from (6R)- and (6S)-6-mesyloxydihydrosphingosine derivatives 7 and 7′, respectiv

A short synthesis of (-)-deoxoprosophylline

Syntheses of (-)-deoxoprosophylline from chiral L-N,N-dibenzylserine (TBDMS) aldehyde is reported. A highly diastereoselective nucleophilic addition of Buechi's Grignard reagent to chiral serinal followed by an intramolecular reductive amination of ω-oxo