268736-70-5

Upstream product

• 1326704-09-9 (2S)-1-[(4-methoxybenzyl)oxy]-6-(trimethylsilyl)hex-5-yn-2-ol 
• 18295-60-8 propargyl magnesium bromide 
• 80910-01-6 (S)-2-[(4-methoxybenzyloxy)methyl]oxirane 
• 824-94-2 p-methoxybenzyl chloride 
• 18295-60-8 allenylmagnesium bromide 

Downstream Products

• 1326704-15-7 2(S)-1-[(4-methoxybenzyl)oxy]hex-5-yn-2-yl acetate 
• 1326704-13-5 (2S)-1-[(4-methoxybenzyl)oxy]hex-5-yn-2-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 1326704-16-8 (2S)-6-iodo-1-[(4-methoxybenzyl)oxy]hex-5-yn-2-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 1326704-17-9 C₃₅H₃₈O₁₂ 
• 400737-16-8 (2S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxy)-4-methoxy-dec-8-yn-1-ol 
• 400737-13-5 tert-Butyl-((S)-1-{(S)-2-[(S)-2-(3,4-dimethoxy-phenyl)-[1,3]dioxolan-4-yl]-1-methoxy-ethyl}-hex-4-ynyloxy)-dimethyl-silane 
• 400736-32-5 (2S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxy)-4-methoxy-dec-8-ynal 
• 268736-72-7 tert-butyl-[1-(4-methoxy-benzyloxymethyl)-hex-4-ynyloxy]-dimethyl-silane 
• 268736-71-6 tert-butyl-[1-(4-methoxy-benzyloxymethyl)-pent-4-ynyloxy]-dimethyl-silane 

Relevant academic research and scientific papers

The first total synthesis of cytopiloyne, an anti-diabetic, polyacetylenic glucoside

The first total synthesis of cytopiloyne 1, a novel bioactive polyacetylenic glucoside isolated from the extract of Bidens pilosa, is described. The structure of cytopiloyne was determined to be 2-β-D-glucopyranosyloxy-1-hydroxytrideca-5,7,9,11-tetrayne by using various spectroscopic methods, but the chirality of the polyyne moiety was unknown. Herein, the convergent synthesis of two diastereomers of cytopiloyne by starting from commercially available 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-diozolane is described. The synthetic sequence involved two key steps: stereoselective glycosylation of the glucosyl trichloroacetimidate with 1-[(4-methoxybenzyl)oxy] hex-5-yn-2-ol to give the desired β-glycoside and the construction of the glucosyl tetrayne skeleton by using a palladium/silver-catalyzed cross-coupling reaction to form the alkyne-alkyne bond, the first such use of this reaction. Comparison between the observed and published characterization data showed the 2R isomer to be the natural product cytopiloyne.

Synthesis of the ABC-ring models of goniodomin A: preference for the unnatural configuration at C11 of the BC-ring in a non-macrocyclic model system

To confirm the natural relative stereochemistry of the ABC-ring of goniodomin A (1), the corresponding three stereoisomeric compounds, (2R,5S,6S,7S,9S,11R,15S)-, (2R,5S,6S,7R,9R,11S,15R)-, and (2R,5S,6S,7R,9R,11R,15S)-isomers (2, 3, and 5, respectively),

Total Synthesis of Apoptolidin: Construction of Enantiomerically Pure Fragments

A general strategy for the total synthesis of the antitumor agent apoptolidin (1) is proposed, and the chemical synthesis of the defined key building blocks (4, 5, 6, 8, and 9) in their enantiomerically pure forms is described. The projected total synthes

Total synthesis of apoptolidin: Part 1. Retrosynthetic analysis and construction of building blocks

No less than 30 stereogenic elements, a highly unsaturated 20-membered macrocyclic system, four carbohydrate units, and unique biological activity, make the natural occurring apoptolidin (1) a challenging synthetic target. The retrosynthetic analysis reve

Synthesis of the macrocyclic core of apoptolidin

The convergent synthesis of the apoptolidin macrocyclic core is described.