Name: (4S,7R,8S,9S,13Z,16S)-4,8-Bis-{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]oxocyclohexadec-13-ene-2,6-dione
Brand: TRC
SKU: TRC-B415780

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Product Overview

Product Code

TRC-B415780

CAS Number

189453-35-8

Product Format

Neat

Molecular Formula

C39 H69 N O5 S Si2

Molecular Weight

720.20

Product Categories

TRC, Macrolides, Pharmaceutical Toxicology Reference Materials

Product Information

Analyte Name

(4S,7R,8S,9S,13Z,16S)-4,8-Bis-{[tert-butyl(dimethyl)silyl]ox

CAS Number

189453-35-8

Molecular Formula

C39 H69 N O5 S Si2

Molecular Weight

720.20

Accurate Mass

719.4435

SMILES

C[C@H]1CCC\C(=C/C[C@H](OC(=O)C[C@H](O[Si](C)(C)C(C)(C)C)C(C)(C)C(=O)[C@H](C)[C@H]1O[Si](C)(C)C(C)(C)C)\C(=C\c2csc(C)n2)\C)\C

InChI

InChI=1S/C39H69NO5SSi2/c1-26-19-18-20-27(2)35(45-48(16,17)38(9,10)11)29(4)36(42)39(12,13)33(44-47(14,15)37(6,7)8)24-34(41)43-32(22-21-26)28(3)23-31-25-46-30(5)40-31/h21,23,25,27,29,32-33,35H,18-20,22,24H2,1-17H3/b26-21-,28-23+/t27-,29+,32-,33-,35-/m0/s1

IUPAC

(4S,7R,8S,9S,13Z,16S)-4,8-bis[[tert-butyl(dimethyl)silyl]oxy]-5,5,7,9,13-pentamethyl-16-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione

Shipping Temperature

Room Temperature

Country of Origin

CANADA

Product Format

Neat

An intermediate in the synthesis of Epothilones. Epothilones are polyketide natural products that inhibit cancer cells by a mechanism similar to paclitaxel, and also are effective against paclitaxel-resistant tumours. Epothilone D is in phase I clinical testing of in patients with advanced solid tumours. Epothilone D is a cytotoxic macrolide that stabilises malignant cells' microtubules and arrests mitosis, a characteristic it shares with other epothilones. They bind to the same hepatic sites as does paclitaxel (Taxol) in a 1:1 stoichiometric ratio of a, b-tubulin heterodimers.

References: Hoee, G., et al.: Pure Appl. Chem., 71, 11, 2019 (1999), Giannakakou, P., et al.: Proc. Natl. Acad. Sci. USA, 97, 2904 (2000)

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(4S,7R,8S,9S,13Z,16S)-4,8-Bis-{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]oxocyclohexadec-13-ene-2,6-dione

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