87604-54-4

Upstream product

• 79364-35-5 (S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 
• 87604-46-4 (2R,3R)-1,2-O-isopropylidene-5-hexene-1,2,3-triol 
• 100-44-7 benzyl chloride 
• 400710-04-5 1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 
• 99493-25-1 diisopropyl (R,R)-2-allyl-1,3,2-dioxaborolane-4,5-dicarboxylate 
• 100-39-0 benzyl bromide 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 

Downstream Products

• 99838-68-3 (2R,3S)-3-(benzyloxy)hex-5-ene-1,2-diol 
• 99838-69-4 (2R,3R)-3-(benzyloxy)hex-5-ene-1,2-diol 
• 122045-93-6 (2R,3R)-3-O-benzyl-1,2-O-isopropylidenepentane-1,2,3,5-tetrol 
• 115887-36-0 (4R)-4-(benzyloxy)-4-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)butan-1-ol 
• 116558-42-0 (3-O-benzyl-2-deoxy-α-D-erythro-pentofuranosyl)iodomethane 
• 698999-98-3 Benzoic acid (2R,3S,5S)-3-benzyloxy-5-iodomethyl-tetrahydro-furan-2-ylmethyl ester 
• 151436-27-0 (2R,3R)-3,5-di-O-benzylpentane-1,2,3,5-tetrol 
• 151385-29-4 (3R,4E)-1,3-di-O-benzylhex-4-ene-1,3,6-triol 
• 151436-26-9 (2R,3R)-3,5-di-O-benzyl-1,2-O-isopropylidenepentane-1,2,3,5-tetrol 
• 151385-30-7 (2R,4E)-1,3-di-O-benzyl-6-O-(methoxymethyl)hex-4-ene-1,3,6-triol 
• 151385-28-3 ethyl (2E,4R)-4,6-dibenzyloxyhex-2-enoate 
• 1012367-48-4 C₂₅H₃₁⁽¹⁵⁾NO₇S 
• 1012367-26-8 methyl (R,E)-4-(benzyloxy)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enyl(tosyl)carbamate 
• 1322779-71-4 (6R,E)-6-(benzyloxy)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-nitro-1-phenylhex-4-en-1-one 

Relevant academic research and scientific papers

Intramolecular ene reactions for methylenecyclohexanol synthesis

Thermally-induced or Lewis acid-mediated intramolecular ene reactions of diastereomeric δ,ε-unsaturated ketones give methylenecyclohexanols in high yield and with excellent diastereoselectivity.

Xylapyrrosides A and B, two rare sugar-morpholine spiroketal pyrrole-derived alkaloids from Xylaria nigripes: Isolation, complete structure elucidation, and total syntheses

Two new [named xylapyrrosides A (1) and B (2)] along with two known [pollenopyrrosides A (3) and B (=acortatarin A, 4)] naturally occurring spirocyclic pyrrole alkaloids were isolated and identified as minor components from the EtOH extract of the dried mycelia of the edible medicinal fungus Xylaria nigripes. Their structures were established by a combination of interpretation of spectroscopic data and single-crystal X-ray diffraction analyses. The isolates possess a unique tricyclic skeleton comprising a common bicyclic 2-formyl-pyrrole-fused morpholine, with a variable ketohexoside ring. This class of alkaloids is quite rare from natural sources. In this study, the total syntheses of compounds 1, 2 and 4 were successfully achieved by two alternative strategies, and three new analogs [named xylapyrrosides A1 (1a), A2 (1b) and B1 (2a)] were also produced. Notably, the total synthesis of such spiroketal alkaloids with a pyranose ring (e.g.,1) was accomplished for the first time. The absolute configurations of the new isolates can be thereafter unequivocally secured by the total syntheses. The above isolated and synthesized spiro-alkaloids were found to show moderate antioxidant effects by preventing the oxidative stress-induced cytotoxicity of A7r5 rat vascular smooth muscle cells (VSMCs).

Stereoselective iodine-induced cyclisation of alkene acetals. Application to the synthesis of 3-deoxy-exo-glycals and substituted tetrahydrofurans

2,5-Substituted tetrahydrofurans have been stereoselectively prepared by a iodine-induced cyclisation of alkene acetals, and the iodo derivatives obtained were transformed into 3-deoxy-exo-glycals and in polyhydroxy substituted tetrahydrofurans.

Enantioselective allyltitanations and metathesis reactions. Application to the synthesis of piperidine alkaloids (+)-sedamine and (-)-prosophylline

An enantioselective synthesis of the piperidine alkaloids (+)-sedamine and (-)-prosophylline is reported. The synthesis of (+)-sedamine has been achieved in 12 steps with an overall yield of 20% from benzaldehyde, and (-)-prosophylline was obtained in 15 steps with an overall yield of 9.2%, starting from D-glyceraldehyde acetonide 14. The key steps are enantioselective allyltitanation reactions and ring-closing or cross-metathesis reactions.

Enantioselective allyltitanation and cross-metathesis. Synthesis of (-)-prosophylline

An enantioselective synthesis of (-)-prosophylline has been accomplished in 15 steps from protected D-glyceraldehyde, with an overall yield of 9.2%, by using two enantioselective allyltitanations and a cross-metathesis reaction as the key-steps.

Enantio- and Diastereocontrolled Synthesis of Chiral 1,2-Diol Derivatives from (R)-2,3-Di-O-isopropylideneglyceraldehyde: endo- and exo-Brevicomin

All four possible stereoisomers of the insect pheromone brevicomin have been prepared from (R)-2,3-di-O-isopropylideneglyceraldehyde (1) on stereocontrolled routes with ee more than 98-99percent.

Enantioselective synthesis of the bottom-half of chlorothricolide

The first enantioselective synthesis of a chlorothricolide intermediate is described. The synthesis features the intramolecular Diels-Alder reaction of tetraene.

ON THE STERIC COURSE OF THE ADDITION OF SOME ORGANOMETALLIC REAGENTS TO (R)-2,3-ISOPROPYLIDENE GLYCERALDEHYDE. SYNTHESIS OF OPTICALLY ACTIVE α-BENZYLOXY ALDEHYDES, ALCOHOLS, CARBOXYLIC ACIDS AND 1,2-DIOLS.

Organo-titanium and organo-zinc reagents were added stereoselectively to (R)-2,3-isopropylidene glyceraldehyde (1) to give the alcohols 2/3, which were converted into the optically active derivatives 4-11.