602301-75-7

Upstream product

• 100-39-0 benzyl bromide 
• 620949-24-8 (2R,4aR,6S,7R,8aS)-6-Hydroxymethyl-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 
• 602301-71-3 (E)-4-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-but-2-enoic acid ethyl ester 
• 602301-72-4 (E)-4-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-but-2-en-1-ol 
• 602301-70-2 (E)-ethyl 4-((2R,4S,5R)-5-hydroxy-2-(4-methoxyphenyl)-1,3-dioxan-4-yl)but-2-enoate 
• 2186-92-7 p-Anisaldehyde dimethyl acetal 
• 602301-65-5 (2R,4aR,6S,7R,8aS)-2-(4-Methoxy-phenyl)-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 

Downstream Products

• 474248-51-6 (2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-ol 
• 474248-53-8 [(2R,4aR,6S,7R,8aS)-6-{3-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-yloxy]-3-phenylsulfanyl-propyl}-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-tert-butyl-dimethyl-silane 
• 602301-94-0 Toluene-4-sulfonic acid (2R,3S,5R,6S)-3-[(2R,4aR,5aS,8R,9S,10aR,11aS)-9-allyl-2-(4-methoxy-phenyl)-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-8-yloxy]-5-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl ester 
• 602301-93-9 Toluene-4-sulfonic acid (2R,3S,5R,6S)-5-benzyloxy-6-benzyloxymethyl-3-[(2R,4aR,5aS,8R,9S,10aR,11aS)-2-(4-methoxy-phenyl)-9-vinyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-8-yloxy]-tetrahydro-pyran-2-ylmethyl ester 
• 602301-82-6 2-[(2R,4aR,5aS,8R,9S,10aR,11aS)-8-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-yloxy]-2-(4-methoxy-phenyl)-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-9-yl]-ethanol 
• 602301-88-2 (2R,4aR,5aS,8R,9S,10aR,11aS)-9-Allyl-8-[(2R,3S,5R,6S)-5-benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-yloxy]-2-(4-methoxy-phenyl)-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene 
• 602301-83-7 (2R,4aR,5aS,8R,9S,10aR,11aS)-8-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-yloxy]-2-(4-methoxy-phenyl)-9-vinyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene 
• 602301-92-8 (2R,4aR,5aS,8R,9S,10aR,11aS)-9-Allyl-8-((2R,3S,5R,6S)-2-allyl-5-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-2-(4-methoxy-phenyl)-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene 
• 602301-91-7 {(2R,3S,5R,6S)-3-[(2R,4aR,5aS,8R,9S,10aR,11aS)-9-Allyl-2-(4-methoxy-phenyl)-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-8-yloxy]-5-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl}-acetonitrile 
• 602301-89-3 {(2R,3S,5R,6S)-3-[(2R,4aR,5aS,8R,9S,10aR,11aS)-9-Allyl-2-(4-methoxy-phenyl)-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-8-yloxy]-5-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl}-methanol 
• 602301-86-0 {(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-[(2R,4aR,5aS,8R,9S,10aR,11aS)-2-(4-methoxy-phenyl)-9-vinyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-8-yloxy]-tetrahydro-pyran-2-yl}-acetonitrile 
• 602301-84-8 {(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-[(2R,4aR,5aS,8R,9S,10aR,11aS)-2-(4-methoxy-phenyl)-9-vinyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-8-yloxy]-tetrahydro-pyran-2-yl}-methanol 
• 602301-87-1 (2R,4aR,5aS,8R,9S,10aR,11aS)-8-((2R,3S,5R,6S)-2-Allyl-5-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-2-(4-methoxy-phenyl)-9-vinyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene 
• 602301-90-6 (2R,4aR,5aS,8R,9S,10aR,11aS)-9-Allyl-8-((2R,3S,5R,6S)-5-benzyloxy-6-benzyloxymethyl-2-vinyl-tetrahydro-pyran-3-yloxy)-2-(4-methoxy-phenyl)-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene 

Relevant academic research and scientific papers

Divergent synthesis of the tetracyclic ethers of 6-X-7-6 ring systems

Ladder-shaped polyether natural products show diverse biological activities with extreme potency. As the initial phase of detailed SAR studies of bioactive polyethers, we set out to construct structurally simple mimics. This paper details the divergent synthesis of 6-X-7-6 tetracycles (X=7, 8, or 9) starting from a simple 6-membered ether. Key reactions in the synthesis include (i) the direct formation of an O,S-acetal by the coupling of an alcohol with an α-chlorosulfide, (ii) the construction of a 7-membered ring by radical cyclization, and (iii) cyclization to the 7, 8 or 9-membered ring via a ring-closing metathesis reaction. The neutral reaction conditions of our strategy enable the synthesis of a wide variety of substrates. The results of this study can be applied for the rapid construction of artificial polyether compounds with diversified molecular shapes and sizes.

Convergent synthesis of trans-fused 6/n/6/6 (n=7, 8) tetracyclic ether system via α-cyano ethers

A convergent method for synthesizing 6/n/6/6 (n=7, 8) tetracyclic ether system via two-rings construction of the central n/6 ring system was developed. The key steps of the present synthesis involve a ring-closing metathesis reaction for the construction of the seven- and eight-membered rings, and reductive etherification for the tetrahydropyrans. Unification of the two fragments through acetal formation, followed by regioselective cleavage of the acetal using TMSCN/TMSOTf in the presence of 2,6-di-tert-butyl-4-methylpyridine, afforded the α-cyano ether, of which the nitrile group was manipulated to give the precursors of the ring-closing reactions.