32780-08-8

Upstream product

• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 100-39-0 benzyl bromide 
• 952057-61-3 N-phenyl-2,2,2-trifluoroacetimidoyl chloride 
• 2930-05-4 (S)-benzyl glycidyl ether 
• 126550-68-3 (R)-1-(benzyloxy)hex-5-en-2-ol 
• 6893-26-1 D-Glutamic acid 
• 21461-84-7 (2S)-tetrahydro-5-oxofuran-2-carboxylic acid 
• 56-86-0 L-glutamic acid 
• 124662-61-9 (S)-5-Benzyloxy-4-hydroxy-1-pentyne 
• 100-51-6 benzyl alcohol 
• 102717-29-3 (5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one 

Downstream Products

• 62396-82-1 (S)-1-benzyloxy-5-methyl-hexane-2,5-diol 
• 72605-52-8 (4S)-(+)-2-phenylseleno-4-benzyloxymethyl-butan-4-olide 
• 571167-73-2 (2S)-tetrahydro-5-hydroxy-2-(benzyloxymethyl)furan 
• 949932-67-6 (S)-5-(benzyloxy)pentane-1,4-diol 
• 147806-54-0 (E)-(S)-7-Benzyloxy-6-hydroxy-2-methyl-hept-2-enoic acid ethyl ester 
• 58526-80-0 D-ribose anilide 
• 87727-31-9 (2S,5R)-tetrahydro-5-<(tert-butyldimethylsilyl)oxy>-2-<(benzyloxy)methyl>furan 
• 87681-37-6 (2S,5S)-tetrahydro-5-<(tert-butyldimethylsilyl)oxy>-2-<(benzyloxy)methyl>furan 
• 92232-54-7 5-O-benzyl-3-deoxy-2-Se-phenyl-2-seleno-D-erythro-pentonic acid γ-lactone 
• 92232-53-6 5-O-benzyl-3-deoxy-2-Se-phenyl-2-seleno-D-threo-pentonic acid γ-lactone 
• 493036-25-2 4-[2-((S)-5-Benzyloxy-4-hydroxy-pentanoylamino)-ethyl]-benzoic acid ethyl ester 
• 147742-29-8 (2S,4S)-4-(3,4,5-Trimethoxy-benzyl)-pentane-1,2,5-triol 
• 70148-33-3 trans-(S)-2-piperonylidene-4-benzyloxymethyl-4-butanolide 
• 85580-13-8 cis-(S)-2-piperonylidene-4-benzyloxymethyl-4-butanolide 

Relevant academic research and scientific papers

First total synthesis of Debilisone C

Total synthesis of Debilisone C, a lactone containing conjugated endiyne has been achieved. The adopted strategy involves the stereoselective construction of the five membered lactone ring and the C20 endiyne chain followed by regioselective coupling of both the parts. The lactone was obtained from the oxidative cleavage of the hydroxy olefin which was derived from the benzyl protected S-epichlorohydrine by regioselective epoxide opening with allyl trimethyl silane in presence of a Lewis acid at -78 °C. Takai olefination, Pd0/Ag1 catalyzed cross-coupling reaction and selective substitution of trimethylsilyl groups were successfully utilized to establish the C20 polyyne chain. The final coupling of both the parts have been carried out by alkyl coupling using LDA in THF-DMPU (1 : 1).

Study on the total synthesis of velbanamine: Chemoselective dioxygenation of alkenes with PIFA via a stop-and-flow strategy

A "stop-and-flow" strategy was developed for the chemoselective dioxygenation of alkenes with a PIFA-initiated cyclization. This method is conceived for the desymmetrization of seco-diene, and a series of substituted 5-hydroxymethyl-γ-lactones were constructed after hydrolysis. This strategy also differentiates terminally substituted alkenes and constitutes a potentially novel synthetic approach for the efficient synthesis toward velbanamine.

Practical synthesis of C1-8 fragment of autolytimycin via a chelation-controlled diastereoselective addition of diisopropenylzinc to α-methoxy aldehyde

The C1-8 fragment of autolytimycin was synthesized via a reliable 10-step route capable of delivering 41% overall yield at multi-gram scale. As a key step, a chelation-controlled isopropenylation of α-oxygenated aldehydes was established with a reagent combination of diisopropenylzinc, magnesium halide, and a dichloromethane/toluene mixed solvent. Cram-chelate isopropenylation products dominated for aldehydes with a small α-substituents, such as -OMe and -OBn groups, while the Felkin product could be obtained with a bulky -OTBS group.

Pyrene intercalating nucleic acids with a carbon linker

We have synthesized a carbon linker analogue of INA (oligonucleotides containing insertions of 1-O-(1-pyrenylmethyl)glycerol). Thermal stability studies showed an increase in melting temperature in favor of the carbon linker analogue. We also synthesized a carbon linker analogue with two pyrenes geminally attached. Fluorescence studies of this intercalating nucleic acid with the pyrene moieties inserted as a bulge showed formation of an excimer band. When a mismatch was introduced at the site of the intercalator, an excimer band was formed for the destabilized duplexes whereas an exciplex band was observed when the stability of the duplex was retained. Copyright Taylor and Francis Group, LLC.

Cyclopropenium-activated cyclodehydration of diols

The dehydrative cyclization of diols to cyclic ethers via cyclopropenium activation is described. Using 2,3-diphenylcyclopropene and methanesulfonic anhydride, a series of 1,4-and 1,5-diols are rapidly cyclized to furnish tetrahydrofurans and tetrahydropyrans in high yield. Eleven total substrates are shown, including a gram scale cyclization of a diterpene derivative.

Benzyl N-phenyl-2,2,2-trifluoroacetimidate: A new and stable reagent for O-benzylation

A new O-benzylation reagent, benzyl N-phenyl-2,2,2-trifluoroacetimidate, has been developed. It even reacts with sterically hindered alcohols and base-sensitive hydroxy esters to afford the corresponding benzyl ethers catalyzed by TMSOTf in 1,4-dioxane. This reagent was more stable than benzyl 2,2,2-trichloroacetimidate, a known benzylation reagent. Copyright

Efficient chirality transfer in the Sml2-mediated cyclization of aldehydo β-alkoxyvinyl sulfoxides: Asymmetric synthesis of 3-hydroxyoxanes

Stereoselective syntheses of 3-hydroxyoxanes were achieved via efficient chirality transfer in the Sml2-mediated cyclization reactions of aldehydo β-alkoxyvinyl sulfoxides.

Synthesis of γ- and δ-lactones from alkynols

The reaction of alkynyl phenyl selenides with p-toluene-sulfonic acid gives rise to a proton-induced ring-closure reaction affording γ- and δ-lactones. Georg Thieme Verlag Stuttgart.

Pectenotoxin-2 synthetic studies. 2. Construction and conjoining of ABC and DE eastern hemisphere subtargets

(Chemical Equation Presented) Practical asymmetric synthesis of aldehyde 2 and tetrazolyl sulfone 3 has allowed for their coupling via Julia olefination to generate 32 as a single product. This substance possesses the entire carbon backbone of the A-E substructure of pectenotoxin-2.

Lactams as EP4 prostanoid receptor agonists. 3. Discovery of N-ethylbenzoic acid 2-pyrrolidinones as subtype selective agents

Two distinct synthetic schemes were applied to access heteroatom-containing α-chain lactams or lactams terminated as aryl acids. The latter lactams were devised using a pharmacophore for EP4 receptor activity. γ-Lactams were characterized for their prostanoid EP receptor affinities and EP 4 activity and found to be selective for the EP2 and EP4 receptors or selective for the EP4 subtype. Benzoic acid 17 displayed enhanced in vivo exposure relative to 3.