105560-79-0

Upstream product

• 917-64-6 methyl magnesium iodide 
• 87205-38-7 (+/-)-(2R,3R)-5-benzyloxy-2,3-epoxy-1-pentanol 
• 73814-97-8 [(2R,3S)-3-(2-Benzyloxy-ethyl)-oxiranyl]-methanol 
• 75-16-1 methylmagnesium bromide 
• 89956-14-9 [3-(2-Benzyloxyethyl)oxiran-2-yl]methanol 
• 934400-52-9 C₁₆H₂₂O₃ 
• 4799-68-2 3-benzyloxypropan-1-ol 
• 89923-31-9 (E)-5-(benzyloxy)pent-2-en-1-ol 
• 70542-83-5 ethyl (2E)-5-(benzyloxy)pent-2-enoate 
• 922493-39-8 C₁₆H₂₂O₃ 
• 95112-81-5 (S)-ethyl 5-benzyloxy-3-hydroxypentanoate 
• 22273-79-6 5-benzyloxy-2-pentyn-1-ol 
• 22273-77-4 ((but-3-yn-1-yloxy)methyl)benzene 
• 781642-34-0 (3E,5R,6S)-8-(benzyloxy)-6-hydroxy-5-methyloct-3-enoic acid methyl ester 

Downstream Products

• 301230-09-1 5-Benzyloxy-1-(tert-butyldiphenylsilanyloxy)-2-methylpentane-3-ol 
• 952677-55-3 (2S,3R,5R,6S)-9-Benzyloxy-3-methoxy-5-methoxymethoxy-2,6-dimethyl-nonan-1-ol 
• 142945-16-2 (2R,3R,5R,6S)-9-Benzyloxy-3-methoxy-5-methoxymethoxy-2,6-dimethyl-nonanal 
• 142945-24-2 (E)-(4R,5R,9S,10R,12R,13S)-16-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4,10-dimethoxy-12-methoxymethoxy-5,9,13-trimethyl-hexadec-7-en-6-one 
• 142945-21-9 (2R,3R,5R,6S)-2-(3-Benzyloxy-propyl)-7-(tert-butyl-diphenyl-silanyloxy)-5-methoxy-3-methoxymethoxy-6-methyl-heptan-1-ol 
• 142945-20-8 4-Benzyl-3-[(2S,3R,5R,6S)-2-(3-benzyloxy-propyl)-7-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5-methoxy-6-methyl-heptanoyl]-oxazolidin-2-one 
• 740836-05-9 [(3S,4R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentyloxymethyl]-benzene 
• 922493-40-1 (2R,3S)-1-[(tert-butyldiphenylsilyl)oxy]-5-benzyloxy-2-methyl-3-pentanol 
• 1391093-64-3 (2R,3S)-5-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-2-methylpentan-3-ol 
• 1391093-66-5 ((2R,3S)-5-(benzyloxy)-3-methoxy-2-methylpentyloxy)(tert-butyl)dimethylsilane 
• 1391093-69-8 (2R,3S)-5-(benzyloxy)-3-methoxy-2-methylpentan-1-ol 
• 1391093-61-0 (2R,3S,4R,5S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-7-(benzyloxy)-3-hydroxy-5-methoxy-2,4-dimethylheptan-1-one 
• 1391093-72-3 (2R,3S,4S,5S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-7-(benzyloxy)-3-(tert-butyl-dimethylsilyloxy)-5-methoxy-2,4-dimethylheptan-1-one 
• 1391093-75-6 (2R,3S,4S,5S)-7-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-5-methoxy-2,4-dimethylheptanal 

Relevant academic research and scientific papers

Molecular insights into azumamide E histone deacetylases inhibitory activity

Azumamide E, a cyclotetrapeptide isolated from the sponge Mycale izuensis, is the most powerful carboxylic acid containing natural histone deacetylase (HDAC) inhibitor known to date. In this paper, we describe design and synthesis of two stereochemical va

A Baylis-Hillman approach to the synthesis of C1-C11 fragment of caribenolide I

Stereoselective synthesis of C1-C11 fragment of caribenolide I, a potent antitumour macrolide isolated from a marine dinoflagellate Amphidinium sp. is described. The key steps rely on asymmetric aldol reactions, to control the absolu

Total synthesis of azumamides A and E

A zoom in on azumamides (2): An efficient synthetic route for two of the newly discovered marine natural products, namely azumamides A and E, has been developed (see picture). The present synthesis was followed by determination of the stereochemical structure of the azumamides. (Chemical Equation Presented)

Synthesis and biological activity of mycalolide analogs

Mycalolide analog 4, consisting only of the side chain of mycalolide B (2), a trisoxazole macrolide of marine origin, was stereoselectively synthesized using Roush crotylboration, an Evans aldol reaction, and a Paterson aldol reaction as key steps. The an

Short synthesis of the 6,6-spiroketal cores of spirofungins A and B

(Matrix Presented) Initial efforts toward the total synthesis of the antifungal antibiotics spirofungins A and B are reported. A short and efficient synthesis of the C9-C20 6,6-spiroketal fragments of both compounds is described. This asymmetric approach

Enantio- and stereocontrolled formation of the bisspiroacetal core of spirolide B

The bisspiroacetal core of spirolide B, a marine natural toxin, was synthesized from triketone 10 via one-step bisspiroacetalization, methylation, and silylation accompanied by isomerization of the C-15 spirocenter. The equilibrium of two isomers under ac

Total synthesis of basiliskamides A and B

(Chemical Equation Presented) The first enantioselective synthesis of the polyketide antibiotics basiliskamides A and B, which exhibit potent in vivo activity against Candida albicans and Aspergillus fumigatus, has been achieved. Serial asymmetric crotylsilane and crotylboronate additions established the C7-C10 stereochemical tetrad. Takai iodoolefination and palladium-mediated cross-coupling were used to install the (Z,E)-vinyl acrylamide. Spectroscopic data is consistent with the assignment of the absolute configurations of the natural products as (7S,8S,9R,10S).

Synthesis and actin-depolymerizing activity of mycalolide analogs

Mycalolide analog 4, consisting only of the side chain of mycalolide B (2), was stereoselectively synthesized and was found to have strong actin-depolymerizing activity.

A total synthesis of the unique tris-oxazole macrolide ulapualide a produced by the marine nudibranch Hexabranchus sanguineus

A total synthesis of ulapualide A (1), whose relative stereochemistry was assigned on the basis of an earlier molecular mechanics study of its hypothetical metal chelated complex 9, is described. The synthesis is based on: i, elaboration of the double fun

Synthetic Studies towards Halichondramides, and Related Novel tris-Oxazole Containing Macrolides from Marine Organisms. A Concise Route to the Keto-triol Formyl Enamine Moiety.

A synthesis of the keto-triol formyl enamine moiety (3) in the marine metabolite halichondramide (1) is described.The synthesis features judicious application of the Evans chiral aldol protocol in combination with the controlled ring opening of chiral α-e