Ficaprel 11

Base Information

• Chemical Name: Ficaprel 11
• CAS No.: 26296-50-4
• Molecular Formula: C₅₅H₉₀O
• Molecular Weight: 767.319
• Mol file: 26296-50-4.mol

Synonyms:2,6,10,14,18,22,26,30,34,38,42-Tetratetracontaundecaen-1-ol,3,7,11,15,19,23,27,31,35,39,43-undecamethyl-, (Z,Z,Z,Z,Z,Z,Z,E,E,E)- (8CI);Cleomeprenol 11; Ficaprenol (C55); Ficaprenol 11; Malloprenol 11; Moraprenol 11

Chemical Property of Ficaprel 11

Chemical Property:

• Boiling Point: 777.0±29.0 °C(Predicted)
• PKA: 14.42±0.10(Predicted)
• PSA: 20.23000
• Density: 0.890±0.06 g/cm3(Predicted)
• LogP: 18.20990

Purity/Quality:

99% ^*data from raw suppliers

Ficaprenol11 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Ficaprel 11

There total 3 articles about Ficaprel 11 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: 96.0%

undecaprenyl acetate → undecaprenol (26296-50-4,59685-00-6,73367-16-5,88200-23-1,20438-12-4,28979-23-9,50426-50-1,11023-57-7,15575-14-1)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; methanol; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1039/d0cc03388j

Reference yield: 65.0%

1-((2Z,6Z,10Z,14Z,18Z,22Z,26Z,30E,34E,38E)-1-benzyloxy-17-tosyl-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-9-yl)sulfonyl-4-methylbenzene (1186313-59-6) → ficaprenol-11 (11023-57-7,15575-14-1,20438-12-4,28979-23-9,50426-50-1,59685-00-6,73367-16-5,88200-23-1,26296-50-4)

Guidance literature:

1-((2Z,6Z,10Z,14Z,18Z,22Z,26Z,30E,34E,38E)-1-benzyloxy-17-tosyl-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-9-yl)sulfonyl-4-methylbenzene; With lithium; ethylamine; In diethyl ether; at -78 ℃; for 1h; Inert atmosphere;

With isoprene; In methanol; diethyl ether; Inert atmosphere;

DOI:10.1016/j.tet.2009.06.032

Reference yield:

ficaprenyl (α-D-glucopyranosyl phosphate) (19427-26-0,66792-12-9,67337-85-3,74033-74-2,84025-33-2,92216-72-3,119239-67-7) → undecaprenol (26296-50-4,59685-00-6,73367-16-5,88200-23-1,20438-12-4,28979-23-9,50426-50-1,11023-57-7,15575-14-1)

Guidance literature:

With sodium hydroxide; In propan-1-ol; at 65 ℃; for 4h; Product distribution; other reaction times;

DOI:10.1016/0008-6215(83)88014-8

upstream raw materials:

1-((2Z,6Z,10Z,14Z,18Z,22Z,26Z,30E,34E,38E)-1-benzyloxy-17-tosyl-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-9-yl)sulfonyl-4-methylbenzene

ficaprenyl (α-D-glucopyranosyl phosphate)

Downstream raw materials:

4-phenylsulfonyl-3,7,11,15,19,23,27,31,35,39,43,47-dodecamethyloctatetraconta-2E,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E,42E,46-dodecaen-1-ol

GlcNAc-pyrophosphorylundecaprenol

Moraprenyl phosphate

Refernces

• 1、 Lee, Yong Joo,Ishiwata, Akihiro,Ito, Yukishige. "Synthesis of undecaprenyl pyrophosphate-linked glycans as donor substrates for bacterial protein N-glycosylation". experimental part. p. 6310 - 6319. Retrieved 2009/12/06.