206660-79-9

Upstream product

• 76-83-5 trityl chloride 
• 13291-18-4 isopropenylmagnesium bromide 
• 129940-50-7 (S)-tritylglycidol 

Downstream Products

• 1007357-46-1 C₃₃H₃₄O₃ 
• 527742-86-5 ((2S,3S)-3-{(2R,3R,4E)-2-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-5-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]pent-4-enyl}oxiran-2-yl)-1-(tert-butyldimethylsilyloxy)methane 
• 445306-64-9 4-[1-[2-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-allyl]-5-(tert-butyl-diphenyl-silanyloxy)-6-methoxymethoxy-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienyloxy]-pentan-2-one 
• 445306-63-8 4-[1-[2-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-allyl]-5-(tert-butyl-diphenyl-silanyloxy)-6-methoxymethoxy-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienyloxy]-pentan-2-ol 
• 445306-66-1 C₅₄H₈₄O₈Si₂ 
• 445306-65-0 2-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-8-(tert-butyl-diphenyl-silanyloxy)-9-methoxymethoxy-11-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-undeca-1,5,10-trien-4-ol 
• 527743-02-8 (S)-2-[(E)-(3S,4S)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methoxymethoxy-6-triethylsilanyloxy-hex-1-enyl]-4-methyl-3,6-dihydro-2H-pyran 
• 445306-59-2 (1E,3S,4S)-4-(tert-butyldiphenylsilanyloxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-6-(triethylsilanyloxy)-hex-1-en-3-ol 
• 445306-70-7 (1E,4S)-4-(tert-butyldiphenylsilanyloxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-6-(triethylsilanyloxy)-hex-1-en-3-one 
• 445306-61-6 (2E,7E,5S,6S)-5-(tert-butyldiphenylsilanyloxy)-6-(methoxymethoxy)-8-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-octa-2,7-dienoic acid N-methoxy-N-methyl-amide 
• 445306-71-8 (3S,4S,5E)-3-(tert-butyldiphenylsilanyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-en-1-ol 
• 445306-60-5 (3S,4S,5E)-3-(tert-butyldiphenylsilanyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-enal 
• 385809-24-5 [(2S),(2S,6S,7E,10S,11S,12E),(2R,6R)]-tert-butyl-(2-{6-[10-(4-methoxybenzyloxy)-6,11-bismethoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylenetrideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}ethoxy)-dimethylsilane 
• 379269-79-1 (1E,6E,3S,4S)-4-(tert-butyldiphenylsilanyloxy)-7-[(4R,6R)-(4,6-dimethyl-[1,3]dioxan-2-yl)]-3-methoxymethoxy-1-[(2S)-(4-methyl-3,6-dihydro-2H-pyran-2-yl)]-hepta-1,6-diene 

Relevant academic research and scientific papers

Synthetic studies towards the total synthesis of providencin

A synthetic approach to assemble the uncommon furylcyclobutane substructure in providencin has been developed starting from a commercially available cyclobutane precursor. Georg Thieme Verlag Stuttgart.

Total synthesis of the microtubule stabilizing antitumor agent laulimalide and some nonnatural analogues: The power of sharpless' asymmetric epoxidation

Three different routes are described for the synthesis of deoxylaulimalide (3), which is the immediate precursor of the marine sponge metabolite laulimalide (1). These routes mainly differ with respect to their ring closing step. Thus, route 1 uses a Still-Gennari olefination, route 2 a Yamaguchi lactonization, and route 3 an intramolecular allylsilane-aldehyde addition for establishing the macrocyclic structure. The unprotected deoxy derivative 3 was subjected to Sharpless' asymmetric epoxidation (SAE). With (R,R)-tartrate the 16,17-epoxide laulimalide (1) is formed selectively, whereas (S,S)-tartrate generates the 21,22-epoxide 142. This demonstrates the high reagent control involved in the SAE process, which in this case is used to achieve high stereo- and regioselectivity. Laulimalide and some derivatives thereof have been tested with respect to antitumor activity and compared to standard compounds paclitaxel and epothilone B.

Synthetic studies toward the microtubule-stabilizing agent laulimalide: Synthesis of the C15-C28 fragment

The C15-C28 fragment of the paclitaxel-like antimicrotubule agent laulimalide has been synthesized in 12 linear steps with an overall yield of 14%. The methyldihydropyran ring of the side chain was efficiently prepared using ring-clo

Synthesis of the C15-C27 fragment of the antitumor agent laulimalide

A stereocontrolled synthesis of the C15-C27 fragment of laulimalide is described. Key features are a divergent-convergent synthesis from (R)-glycidol, an interesting formation of a trisubstituted double bond via ring closing metathesis with Grubbs' ruthen