(Z,Z)-farnesyl bromide

Base Information

• Chemical Name: (Z,Z)-farnesyl bromide
• CAS No.: 24163-93-7
• Molecular Formula: C₁₅H₂₅Br
• Molecular Weight: 285.267
• Mol file: 24163-93-7.mol

Synonyms:(Z,Z)-farnesyl bromide

Chemical Property of (Z,Z)-farnesyl bromide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (Z,Z)-farnesyl bromide

There total 31 articles about (Z,Z)-farnesyl bromide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

Farnesol (106-28-5) → farnesyl bromide (24163-93-7,24163-94-8,56881-57-3,6874-67-5,28290-41-7)

Guidance literature:

With pyridine; phosphorus tribromide; In diethyl ether; at 5 ℃; for 3h; Darkness;

DOI:10.1002/jlcr.3083

Reference yield: 96.0%

(+/-)-nerolidol (7212-44-4) → farnesyl bromide (24163-93-7,24163-94-8,28290-41-7,56881-57-3,6874-67-5)

Guidance literature:

With phosphorus tribromide; triethylamine; In toluene; at -5 - 23 ℃; for 1.33333h; Product distribution / selectivity;

Reference yield: 91.0%

farnesol (4602-84-0) → farnesyl bromide (24163-93-7,24163-94-8,28290-41-7,56881-57-3,6874-67-5)

Guidance literature:

With phosphorus tribromide; triethylamine; In toluene; at -5 ℃; for 2h; Product distribution / selectivity;

upstream raw materials:

(+/-)-nerolidol

(S)-(+)-nerolidol

farnesol

pyridine

Downstream raw materials:

6,10,14-trimethyl-5,9,13-pentadecatrien-2-one

squalene

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

1,4-Bis-benzyloxy-2-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyl-28-(toluene-4-sulfonyl)-tetraconta-2,6,10,14,18,22,26,30,34,38-decaenyl]-5,6-dimethoxy-3-methyl-benzene

Refernces

• 1、 Castro, Alfredo,Erickson, Sandra K.,Shechter, Ishaiahu,Spencer, Thomas A.. "Synthesis and biological evaluation of nonionic prenyl, geranyl, and farnesyl diphosphate surrogates". . p. 242 - 250. Retrieved 1996.
• 2、 Rinkel, Jan,Lauterbach, Lukas,Dickschat, Jeroen S.. "A Branched Diterpene Cascade: The Mechanism of Spinodiene Synthase from Saccharopolyspora spinosa". . p. 452 - 455. Retrieved 2019.
• 3、 Dickschat, Jeroen S.,Quan, Zhiyang. "On the mechanism of ophiobolin F synthase and the absolute configuration of its product by isotopic labelling experiments". . p. 6072 - 6076. Retrieved 2020.
• 4、 Dejon, Lisa,Speicher, Andreas. "Synthesis of aurachin D and isoprenoid analogues from the myxobacterium Stigmatella aurantiaca". . p. 6700 - 6702. Retrieved 2013.
• 5、 Naumann, Eva Christine,G?ring, Stefan,Ogorek, Isabella,Weggen, Sascha,Schmidt, Boris. "Membrane anchoring γ-secretase modulators with terpene-derived moieties". . p. 3852 - 3856. Retrieved 2013.
• 6、 Biller,Forster,Gordon,Harrity,Scott,Ciosek Jr.. "Isoprenoid (phosphinylmethyl)phosphonates as inhibitors of squalene synthetase". . p. 1869 - 1871. Retrieved 1988.
• 7、 Hoshino, Tsutomu,Kumai, Yuko,Sato, Tsutomu. "Reviewing the polyolefin cyclization reaction of the C35 polyprene catalyzed by squalene-hopene cyclase". . p. 2091 - 2100. Retrieved 2009.
• 8、 Feld, Birte K.,Weiss, Gregory A.. "Convenient methods for the synthesis of P1-farnesyl-P 2-indicator diphosphates". . p. 1665 - 1667. Retrieved 2006.
• 9、 -. "Protein degradation targeting chimeric compound, preparation method and medical application thereof". Paragraph 0218-0219; 0222-0223. . Retrieved 2021/03/31.
• 10、 -. "CHINONE-, HYDROCHINOME- AND NAPHTHOCHINONE-ANALOGUES OF VATIQUIONE FOR TREATMENT OF MITOCHONDRIAL DISORDER DISEASES". Page/Page column 187. . Retrieved 2021/04/10.