457100-61-7

Basic information

• Product Name: (S)-5-(4-methoxyphenoxy)-hexan-1-ol
• Synonyms: (S)-5-(4-methoxyphenoxy)-hexan-1-ol
• CAS NO: 457100-61-7
• Molecular Weight: 224.3
• Mol File: 457100-61-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-5-(4-methoxyphenoxy)-hexan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-5-(4-methoxyphenoxy)-hexan-1-ol(457100-61-7)
• EPA Substance Registry System: (S)-5-(4-methoxyphenoxy)-hexan-1-ol(457100-61-7)

Safety Data

• Hazardous Substances Data: 457100-61-7(Hazardous Substances Data)

Upstream product

• 17397-29-4 (2R)-hex-5-en-2-ol 
• 150-76-5 4-methoxy-phenol 
• 457100-60-6 ethyl (E)-(S)-5-(4-methoxyphenoxy)-hex-2-enoate 
• 717124-34-0 (S)-3-(4-methoxyphenoxy)-butan-1-ol 
• 101933-95-3 (S)-1-methylprop-2-enyl 4-methoxyphenyl ether 

Downstream Products

• 457100-62-8 5-[(S)-5-(4-methoxyphenoxy)hexyl-1-sulfonyl]-1-phenyl-1H-tetrazole 
• 457100-63-9 ethyl (E)-(R)-4-(tert-butyldimethylsilyloxy)-{(1R,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-[(E)-(S)-6-(4-methoxyphenoxy)hept-1-enyl]cyclopentyl}but-2-enoate 
• 20350-15-6 (+)-brefeldin A 

Relevant articles and documents

Total synthesis of the antitumor macrolides, (+)-brefeldin A and 4-epi-brefeldin A from d-glucose: Use of the Padwa anionic allenylsulfone [3 + 2]-cycloadditive elimination to construct trans-configured chiral cyclopentane systems

A new synthesis of (+)-brefeldin A is reported via Padwa allenylsulfone [3 + 2]-cycloadditive elimination. Cycloadduct 13 was initially elaborated into iodide 27, which, following treatment with Zn, gave aldehyde 28 whose C(9) stereocenter was epimerized. Further elaboration into enoate 38 and Julia-Kocienski olefination with 5 subsequently afforded 39, which was deprotected at C(1) and O(15). Yamaguchi macrolactonization of the seco-acid thereafter afforded a macrocycle that underwent O-desilylation and inversion at C(4) to give (+)-brefeldin A following deprotection.

4-Aryloxybutenolides as "chiral aldehyde" equivalents: An efficient enantioselective synthesis of (+)-brefeldin A

4-(2′-Naphthoxy)-2-butenolide, readily available with high enantiopurity by a dynamic kinetic asymmetric transformation (DYKAT) of racemic 4-acyloxybutenolides (available in two steps from furfural), serves as an excellent chiral building block where the naphthoxy group strongly directs the stereochemistry of cycloadditions to the double bond. Notably, the cycloadditions of trimethylenemethanepalladium intermediates which do not exhibit good diastereoselectivity in additions to acceptors that possess many common and important chiral auxiliaries undergo cycloadditions with excellent regio- and stereocontrol. The utility of this process set the stage for an efficient new synthesis of (+)-brefeldin A, a compound of growing pharmacological significance. This synthesis also highlights the Pd-catalyzed DYKAT of crotyl carbonate to create the remote stereocenter. A new two-step method to convert aldehydes to δ-hydroxy-E-α,β-enoates is also outlined. Copyright