210690-85-0

Basic information

• Product Name: 4-[(1E,3S,5Z,8R/S,10S)-3,11-Bis-{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-undeca-1,5-dienyl]-2-methyl-1,3-thiazole
• Synonyms: 4-[(1E,3S,5Z,8R/S,10S)-3,11-Bis-{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-undeca-1,5-dienyl]-2-methyl-1,3-thiazole;4-[(1E,3S,5Z,10S)-3,11-Bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-2,6,10-triMethyl-1,5-undecadien-1-yl]-2-Methyl-thiazole
• CAS NO: 210690-85-0
• Molecular Formula: C₃₀H₅₇NO₂SSi₂
• Molecular Weight: 552.01508
• Product Categories: Chiral Reagents
• Mol File: 210690-85-0.mol

Chemical Properties

• Boiling Point: 550.105°C at 760 mmHg
• Flash Point: 286.494°C
• Appearance: /
• Density: 0.94g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.492
• Solubility: Chloroform, Dichloromethane, Ethanol, Ethyl Acetate, Methanol, Toluene
• PKA: 2.73±0.10(Predicted)
• CAS DataBase Reference: 4-[(1E,3S,5Z,8R/S,10S)-3,11-Bis-{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-undeca-1,5-dienyl]-2-methyl-1,3-thiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(1E,3S,5Z,8R/S,10S)-3,11-Bis-{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-undeca-1,5-dienyl]-2-methyl-1,3-thiazole(210690-85-0)
• EPA Substance Registry System: 4-[(1E,3S,5Z,8R/S,10S)-3,11-Bis-{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-undeca-1,5-dienyl]-2-methyl-1,3-thiazole(210690-85-0)

Safety Data

• Hazardous Substances Data: 210690-85-0(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

InChI:InChI=1/C30H57NO2SSi2/c1-23(16-15-17-24(2)21-32-35(11,12)29(5,6)7)18-19-28(33-36(13,14)30(8,9)10)25(3)20-27-22-34-26(4)31-27/h18,20,22,24,28H,15-17,19,21H2,1-14H3/b23-18-,25-20+/t24-,28-/m0/s1

Upstream product

• 113453-27-3 1-(tert-Butyldimethylsilyl) [(2S)-5-iodo-2-methylpentenyl] ether 
• 210690-66-7 tert-Butyldimethylsilyl {(1S,3Z)-4-iodo-1-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-3-pentenyl} ether 
• 308357-81-5 4-[(1E,3S,5Z,8R/S,10S)-3,11-bis{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-8-(phenylsulfonyl)undeca-1,5-dienyl]-2-methyl-1,3-thiazole 
• 226940-57-4 4-[(1E,5E)-(3S,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-6-chloromethyl-2,10-dimethyl-undeca-1,5-dienyl]-2-methyl-thiazole 
• 39238-07-8 4-(chloromethyl)-2-methyl-1,3-thiazole 
• 121587-29-9 (3S)-3-methyl-1-phenylsulfonylbutan-4-ol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 164264-14-6 (3S)-3-[(1,1-Dimethylethyl)dimethylsilyloxy]-oxolan-2-one 
• 188899-14-1 (3S,4E)-3-(tert-butyldimethylsilyloxy)-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-ol 
• 188730-08-7 (3S,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-al 
• 218615-21-5 (3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-hydroxypentan-2-one 
• 218613-98-0 (-)-(3S)-4-{[tert-butyl(dimethyl)silyl]oxy}-3-methylbutyl phenyl sulfone 
• 218614-07-4 4-((1E,3S,5Z)-3-{[tert-butyl(dimethyl)silyl]oxy}-7-iodo-2,6-dimethylhepta-1,5-dienyl)-2-methyl-1,3-thiazole 
• 218614-16-5 (-)-(2Z,5S,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dien-1-ol 

Downstream Products

• 210690-99-6 (2S,6Z,9S,10E)-9-[(1,1-Dimethylethyl)dimethylsilyloxy]-11-(2-methylthiazol-4-yl)-2,6,10-trimethyl-undeca-6,10-dien-1-ol 
• 152044-54-7 epothilone B 
• 189453-35-8 (4S,7R,8S,9S,13Z,16S,1'E)-4,8-di-tert-butyldimethylsilyloxy-5,5,7,9,13-pentamethyl-16-[1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-1-oxa-13-cyclohexadecene-2,6-dione 
• 189453-10-9 epothilone D 
• 193146-53-1 (5S,8R,9S,10S,17S,Z)-9-(tert-butyldimethylsilyloxy)-5-(2-hydroxyethyl)-2,2,3,3,6,6,8,10,14,19,19,20,20-tridecamethyl-17-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,18-dioxa-3,19-disilahenicos-14-en-7-one 
• 193146-51-9 (7S,10R,11S,12S,19S,Z)-7,11-bis(tert-butyldimethylsilyloxy)-2,2,3,3,8,8,10,12,16,21,21,22,22-tridecamethyl-19-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,20-dioxa-3,21-disilatricos-16-en-9-one 
• 193146-49-5 (7S,10R,11S,12S,19S,Z)-7-(tert-butyldimethylsilyloxy)-11-hydroxy-2,2,3,3,8,8,10,12,16,21,21,22,22-tridecamethyl-19-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,20-dioxa-3,21-disilatricos-16-en-9-one 
• 193146-63-3 (12Z,16E)-(3S,6R,7S,8S,15S)-3,7,15-tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienoic acid 
• 193146-26-8 (3S,6R,7S,8S,12Z,15S,16E)-3,7-bis{[tert-butyl(dimethyl)silyl]oxy}-15-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid 
• 219989-84-1 ixabepilone 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF (1S,3S,7S,10R,11S,12S,16R)-7,11-DIHYDROXY-8,8,10,12,16-PENTAMETHYL-3-[(1E)-1-METHYL-2-(2-METHYL-4-THIAZOLYL)ETHENYL]-17-OXA-4-AZABICYCLO[14.1.0]HEPTADECANE-5,9-DIONE AND INTERMEDIATES THEREOF

The present invention relates to an improved process for the preparation of (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-methyl-2-(2- methyl-4-thiazolyl)ethenyl]- 17-oxa-4-azabicyclo[ 14.1.0]heptadecane-5,9-dione represented by the following structural formula I and intermediates thereof. The present invention also provides novel intermediate compounds useful for the preparation of compound of formula I and its intermediates.

Synthesis of (Z)-Trisubstituted olefins by decarboxylative Grob-Type fragmentations: Epothilone D, discodermolide, and peloruside A

Methyl-branched (Z)-trisubstituted olefins are found in many polyketides with interesting biological activity, such as epothilone D (1), discodermolide (3), and peloruside A (2). Despite the employment of numerous different strategies, this motif has often been the weak point in total synthesis. Thus, we present a novel hydroxideinduced Grob-type fragmentation as an easy access to trisubstituted olefins. In our case, β-mesyloxy δ-lactones with three stereogenic centers were chosen whose fragmentation underlies a high stereoelectronic control. Major challenges in the syntheses were the instailation of quaternary stereocenters, achieved by enzymatic desymmetrization of meso-diesters and by aluminiumpromoted stereoselective rearrangement of chiral epoxides, respectively. Different aldol strategies were developed for the formation of the fragmentation precursors. Additionally a short survey about nucleophilic additions to aldehydes with quaternary α-centers is presented.

Method for producing epothilone B and derivatives, and intermediate products for this method

The invention relates to a method for producing epothilone B and derivatives, and to intermediate products for this method. According to the novel method, the epothilone B or derivatives are produced in high yields from the C1-C6, C7-C10 and C11-C20-fragm

Intermediates for the synthesis of epothilones and methods for their preparation

The invention relates to a method of synthesis for a compound of formula (I), wherein R is a heterocyclyl moiety and X1, X2, X3and X4are, independently of each other, protecting groups, which is appropriate for the synthesis of epothilone B and desoxyepothione B.

Total Syntheses of Epothilones B and D

Total syntheses of the microtubule stabilizing antitumor drugs epothilone B and D are described, starting from optically pure (S)-malic acid and methyl (R)-3-hydroxy-2-methylpropionate. The synthesis is highly convergent by coupling the three fragments C1-C6 (fragment D), C7-C10 (fragment C), and C11-C21 (fragment B). Key steps are two stereoselective Wittig type olefinations to generate the 12,13- and 16,17-double bonds, an enantioselective Mukaiyama aldol addition to synthesize fragment D, and a sulfone anion allyl iodide alkylation to connect fragments B and C. Finally fragment D was attached to the B + C fragment via aldol addition.

Synthesis of 16-desmethylepothilone B: Improved methodology for the rapid, highly selective and convergent construction of epothilone B and analogues

During a synthesis of 16-desmethylepothilone B new methods for the convergent and highly stereoselective synthesis of epothilone B and analogues were developed.

Syntheses of (-)-epothilone B

Two efficient routes for the total synthesis of (-)-epothilone B are reported. One strategy is based on ring-closing metathesis, and a second synthesis on a macrolactonization. The key fragments are available on large scale to provide sufficient material for biological tests. Thiazole fragment 4 was obtained by an improved route starting from (S)-malic acid. The first synthesis is based on our preceding paper. The critical trisubstituted double bond C12-13 in our second approach was constructed by a highly efficient Pd- mediated coupling reaction. Ring closure was achieved by macrolactonization.

Easy access to the epothilone family - Synthesis of epothilone B

An easy access to four out of five naturally occurring epothilones (A- E, 1-5) is reported. Key steps are an enantioselective Mukaiyama type aldol reaction, (E)- and (Z)-selective olefinations, and a sulfone alkylation.

Synthesis of epothilones: Stereoselective routes to epothilone B

In connection with our studies of the total syntheses of epothilones we report our efforts on the syntheses of epothilone B using a macro-lactonization and a metathesis approach. Key reaction for the solution of the acyclic stereoselection is a stereoselective aldol reaction.