104265-24-9

Usage

Chemical Properties

Colorless liquid

Upstream product

• 1245644-03-4 (R)-methyl 5-(benzyloxy)-4-methyl-2-oxopentanoate 
• 1413429-24-9 (R)-methyl 5-(benzyloxy)-4-methyl-2-(((methylsulfonyl)oxy)imino)pentanoate 
• 63930-49-4 (R)-3-(benzyloxy)-2-methylpropan-1-ol 
• 143-33-9 sodium cyanide 
• 128693-46-9 Methanesulfonic acid (S)-3-benzyloxy-2-methyl-propyl ester 

Downstream Products

• 273733-97-4 (3S,5S)-3-[(R)-3-((2R,6R)-6-Allyl-3,6-dihydro-2H-pyran-2-yl)-2-methyl-propyl]-3-benzenesulfonyl-5-(4-methoxy-benzyloxymethyl)-dihydro-furan-2-one 
• 273733-98-5 (2S,4S)-2-[(R)-3-((2R,6R)-6-Allyl-3,6-dihydro-2H-pyran-2-yl)-2-methyl-propyl]-2-benzenesulfonyl-5-(4-methoxy-benzyloxy)-pentane-1,4-diol 
• 945001-95-6 (R)-4-(benzyloxy)-3-methylbutanimidamide 
• 394657-50-2 4-{6-[10-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-11-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2-trimethylsilanyl-ethyl ester 
• 1026853-78-0 (3E,9E)-(1R,7S,11S,15S,17R)-7-[(E)-(S)-1-(4-Methoxy-benzyloxy)-3-((R)-4-methyl-5,6-dihydro-2H-pyran-2-yl)-allyl]-11-methoxymethoxy-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one 
• 312695-84-4 [bis-(2,2,2-trifluoro-ethoxy)-phosphoryl]-acetic acid 7-{3-[6-(2-hydroxy-ethyl)-3,6-dihydro-2H-pyran-2-yl]-2-methyl-propyl}-1-[1-(4-methoxy-benzyloxy)-3-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyl]-5-methoxymethoxy-octa-3,7-dienyl ester 
• 312695-95-7 [bis-(2,2,2-trifluoro-ethoxy)-phosphoryl]-acetic acid 1-[1-(4-methoxy-benzyloxy)-3-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyl]-5-methoxymethoxy-7-{2-methyl-3-[6-(2-oxo-ethyl)-3,6-dihydro-2H-pyran-2-yl]-propyl}-octa-3,7-dienyl ester 
• 349539-71-5 4-{6-[11-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-10-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-ynoic acid methyl ester 
• 394657-63-7 C₄₄H₆₂Br₂O₈ 

Relevant academic research and scientific papers

Facile and efficient synthesis of (r)-4-(benzyloxy)-3-methylbutanenitrile: Toward developing a versatile chiral building block

A practical synthesis of (R)-4-(benzyloxy)-3-methylbutanenitrile, a potential chiral building block, from the corresponding α-keto ester in high yield and large scale was presented. A practical synthesis of (R)-4-(benzyloxy)-3-methylbutanenitrile, a potential chiral building block, from the corresponding α-keto ester in high yield and large scale was presented. Copyright

Total synthesis of microtubule-stabilizing agent (-)-laulimalide

An enantioselective first total synthesis of laulimalide (1) is described. Laulimalide, a remarkably potent antitumor macrolide, has been isolated from the Indonesian sponge Hyattella sp. and the Okinawan sponge Fasciospongia rimosa. Laulimalide represents a new class of antitumor agents with significant clinical potential. The synthesis is convergent and involved the assembly of C3-C16 segment 4 and C17-C28 segment 5 by Julia olefination. The sensitive C2-C3 cis-olefin functionality was installed by Yamaguchi macrolactonization of a hydroxy alkynic acid followed by hydrogenation of the resulting alkynoic lactone over Lindlar's catalyst. Initial attempts of intramolecular Still's variant of Horner - Emmons olefination between the C19-phosphonocetate and C3-aldehyde provided a 1:2 mixture of cis- and trans-macrolactones. The trans-isomer was photo-isomerized to a mixture of cis- and trans-isomers. The other key steps involved ring-closing olefin metathesis to construct both dihydropyran units, stereoselective anomeric alkylation to functionalize the dihydropyran ring, stereoselective reduction of the resulting alkynyl ketone to set the C20-hydroxyl stereochemistry, and a novel Julia olefination protocol for the installation of the C13-exomethylene unit. The sensitive epoxide at C16-C17 was introduced in a highly stereoselective manner by Sharpless epoxidation at the final stage of the synthesis.

An enantioselective synthesis of the C2-C16 segment of antitumor macrolide laulimalide

An enantioselective synthesis of the C2-C16 segment of the novel antitumor agent laulimalide is described. The key steps involve a highly diastereoselective allylation, ring-closing olefin metathesis of a homoallylic alcohol derived acrylate ester, a stereoselective anomeric alkylation and an elaboration of an exo-methylene unit by a Julia olefination reaction. (C) 2000 Elsevier Science Ltd.