197230-20-9

Basic information

• Product Name: (R)-7-azido-1-hepten-4-ol
• Synonyms: (R)-7-azido-1-hepten-4-ol
• CAS NO: 197230-20-9
• Molecular Weight: 155.2
• Mol File: 197230-20-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (R)-7-azido-1-hepten-4-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-7-azido-1-hepten-4-ol(197230-20-9)
• EPA Substance Registry System: (R)-7-azido-1-hepten-4-ol(197230-20-9)

Safety Data

• Hazardous Substances Data: 197230-20-9(Hazardous Substances Data)

Upstream product

• 99545-47-8 4-azidobutanal 
• 85134-98-1 (-)-B-methoxydiisopinocampheylborane 
• 1730-25-2 allylmagnesium bromide 
• 85116-38-7 (+)-diisopinocampheylallylborane 

Relevant articles and documents

Development of a double allylboration reagent targeting 1,5-syn-(E)-diols: Application to the synthesis of the C(23)-C(40) fragment of tetrafibricin

Interest in the synthesis of the C(23)-C(40) fragment 2 of tetrafibricin prompted us to develop a new method for the synthesis of 1,5-syn-(E)-diols. Toward this end, the kinetically controlled hydroboration of allenes 6, 33, ent-39, 42, and 45 with the Soderquist borane 25R were studied. Tetrabutylammonium allenyltrifluoroborate 45 gave superior results and was utilized in a double allylboration sequence with two different aldehydes to provide the targeted 1,5-syn-(E)-diols in generally high yields (72-98%), and with high enantioselectivity (>95% ee), diastereoselectivity (dr >20:1), and (E)/(Z) selectivity (>20:1). This new method was applied to the synthesis of the C(23)-C(40) fragment 2 of tetrafibricin.