127943-53-7

Usage

InChI:InChI=1/C33H55NO8/c1-10-11-12-20(4)31(42-33(34)40)24(8)29(37)22(6)16-18(2)15-21(5)28(36)19(3)13-14-26(35)17-27-23(7)30(38)25(9)32(39)41-27/h10-15,19-31,35-38H,1,16-17H2,2-9H3,(H2,34,40)/b12-11-,14-13-,18-15-/t19-,20-,21-,22-,23-,24-,25+,26+,27-,28-,29+,30-,31-/m0/s1

Upstream product

• 261968-26-7 methyl (2R,3S,4S,5S,7S,8Z,10S,11S,12S,13Z,16S,17R,18S,19S,20S,21Z)-3,11,17-tris-(t-butyldimethylsilyloxy)-5,7-dihydroxy-19-(carbamoyloxy)-2,4,10,12,14,16,18,20-octamethyl-tetracosa-8,13,21,23-tetraenoate 
• 261968-27-8 3,11,17-O-tris-(tert-butyldimethylsilyl)discodermolide 
• 443761-81-7 (2R,3S,4S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentanal 
• 457623-10-8 4R,6-bis(tert-butyldimethylsilanyloxy)-3S,5S-dimethylhex-1-ene 
• 106296-58-6 (2S,3R,4S)-1-(tert-butyldimethylsilyloxy)-2,4-dimethylhex-5-en-3-ol 
• 252342-44-2 (2S,4S,5S)-4-[(Z)-(1R,2R,3S,7S,8R,9S)-2,8-bis(tert-butyldimethylsilanyloxy)-10-(4-methoxybenzyloxy)-1,3,5,7,9-pentamethyldec-5-enyl]-2-(4-methoxyphenyl)-5-methyl-[1,3]dioxane 
• 252342-52-2 (Z)-(2S,3R,4S,8S,9R,10R)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4,6,8-tetramethyl-undec-5-en-1-ol 
• 252342-50-0 tert-Butyl-((1S,2R)-3-iodo-1-{(R)-1-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-ethyl}-2-methyl-propoxy)-dimethyl-silane 
• 303727-87-9 (2R,3S,4S)-3-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentanoic acid N-methoxy-N-methyl-amide 
• 252342-49-7 (2R,3S,4S)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentanoic acid methoxymethylamide 
• 132969-62-1 (2'R,3'S,4'S,4R,5S)-3-[3'-hydroxy-5'-(4-methoxyphenyl)methoxy-2',4'-dimethylpentanoyl]-5-phenyl-4-methyl-2-oxazolidinone 
• 852049-61-7 carbamic acid 3-(tert-butyl-dimethyl-silanyloxy)-14-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-9,13-bis-methoxymethoxy-2,4,6,8,10-pentamethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester 
• 261968-25-6 methyl (2R,3S,4R,7S,8Z,10S,11S,12S,13Z,16S,17R,18S,19S,20S,21Z)-3,11,17-tris-(t-butyldimethylsilyloxy)-19-(carbamoyloxy)-7-hydroxy-2,4,10,12,14,16,18,20-octamethyl-5-oxo-tetracosa-8,13,21,23-tetraenoate 

Related news

Design, synthesis and biological evaluation of a simplified fluorescently labeled discodermolide (cas 127943-53-7) as a molecular probe to study the binding of discodermolide (cas 127943-53-7) to tubulin08/20/2019

The design, synthesis, and biological evaluation of a simplified fluorescently labeled discodermolide analogue possessing a dimethylaminobenzoyl fluorophore has been achieved. Stereoselective Suzuki coupling and Horner–Wadsworth–Emmons reaction comprised the key tactics for its construction. T...detailed

Relevant academic research and scientific papers

A second-generation total synthesis of (+)-discodermolide: The development of a practical route using solely substrate-based stereocontrol

(Chemical Equation Presented). A novel total synthesis of the complex polyketide (+)-discodermolide, a promising anticancer agent of sponge origin, has been completed in 7.8% overall yield over 24 linear steps, with 35 steps altogether. This second-genera

Large-Scale Synthesis of the Anti-Cancer Marine Natural Product (+)-Discodermolide. Part 5: Linkage of Fragments C1-6 and C 7-24 and Finale

The finale of the large-scale preparation of 60 g of the highly complex marine natural product, (+)-discodermolide (1), using a hybridized Novartis-Smith-Paterson synthetic route is presented. This contribution, which is the concluding part of a five-part series, highlights a reagent-controlled stereoselective boron enolate aldol reaction between 2 and 3 forming the C7 hydroxyl-bearing stereocenter, selective reduction of 4a to generate the 1,3-anti-diol 5, and a global deprotection and concomitant lactonization leading to (+)-discodermolide (1). A novel procedure for converting the minor epimeric aldol adduct 4b into discodermolide using a five-step sequence is also described. This large-scale synthesis of discodermolide involved 39 steps (26 steps in the longest linear sequence) and several chromatographic purifications and delivered sufficient material for early-stage human clinical trials.

α-Oxygenated crotyltitanium and dyotropic rearrangement in the total synthesis of discodermolide

(Chemical Equation Presented) A complete strategy: The total synthesis of discodermolide relies on the elaboration of syn-anti stereotriads linked to a Z-O-enecarbamate group, its direct transformation into the terminal Z diene, and stereocontrolled gener

Total synthesis of discodermolide: Optimization of the effective synthetic route

An efficient and modulable total synthesis of discodermolide (DDM), a unique marine anticancer polyketide is described including related alternative synthetic approaches. Particularly notable is the repeated application of a crotyltitanation reaction to yield homoallylic (Z)-O-ene-carbamate alcohols with excellent selectivity. Advantage was taken of this reaction not only for the stereocontrolled building of the syn-anti methyl-hydroxy- methyl triads of DDM, but also for the direct construction of the terminal (Z)diene. Of particular interest is also the installation of the C13=C14 (Z)-double bond through a highly selective dyotropic rearrangement. The preparation of the middle C8-C14 fragment in two sequential stages and its coupling to the C1-C7 moiety was a real challenge and required careful optimization. Several synthetic routes were explored to allow high and reliable yields. Due to the flexibility and robust character of this approach, it might enable a systematic structural variation of DDM and, therefore, the elaboration and exploration of novel discodermolide structural analogues.

Intermediates for the synthesis of polypropionate antibiotics

The invention relates to intermediate compounds of the formula wherein R1 is H or a protecting group, R2 and R3 each independently represent H, methyl, or a leaving group, provided that at least one, but not both, of Rsup

Total synthesis of (+)-discodermolide: A highly convergent fourth-generation approach

(Chemical Equation Presented) A highly convergent, fourth-generation total synthesis of (+)-discodermolide (1), with a longest linear sequence of 17 steps and an overall yield of 9.0%, has been achieved. Highlighting the strategy is the efficient construc

SYNTHETIC TECHNIQUES AND INTERMEDIATES FOR POLYHYDROXY DIENYL LACTONES AND MIMICS THEREOF

Synthetic methods and intermediates useful in the preparation of lactone containing compounds such as discodermolide and compounds which mimic the chemical or biological activity of discodermolide are provided.

SYNTHESIS OF DISCODERMOLIDE

The invention relates to a process for preparing discodermolide, for preparing intermediates for the manufacture of discodermolide and discodermolide analogues and to the intermediates obtained during the process. Wherein the process proceeds via a tetrae

Total synthesis of (+)-discodermolide: An improved endgame exploiting a Still-Gennari-type olefination with a C1-C8 β-ketophosphonate fragment

(Chemical Equation Presented) An improved, third-generation, total synthesis of (+)-discodermolide, a potent microtubule-stabilizing anticancer agent of marine sponge origin, is achieved in 11.1% yield over 21 steps. Key steps include a Still-Gennari HWE

Total synthesis of the potent microtubule-stabilizing agent (+)-discodermolide

The total synthesis of the potent microtubule-stabilizing, antimitotic agent (+)-discodermolide is described. The convergent synthetic strategy takes advantage of the diastereoselective alkylation of a ketone enolate to establish the key C15-C16 bond. The synthesis is amenable to preparation of gram-scale quantities of (+)-discodermolide and analogues.