1220512-56-0

Basic information

• Product Name: (5R,7R)-5,7-bis{[(tert-butyl)(dimethyl)silyl]oxy}-1-(4-hydroxyphenyl)icosan-3-one
• Synonyms: (5R,7R)-5,7-bis{[(tert-butyl)(dimethyl)silyl]oxy}-1-(4-hydroxyphenyl)icosan-3-one
• CAS NO: 1220512-56-0
• Molecular Weight: 649.158
• Mol File: 1220512-56-0.mol

Chemical Properties

• CAS DataBase Reference: (5R,7R)-5,7-bis{[(tert-butyl)(dimethyl)silyl]oxy}-1-(4-hydroxyphenyl)icosan-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (5R,7R)-5,7-bis{[(tert-butyl)(dimethyl)silyl]oxy}-1-(4-hydroxyphenyl)icosan-3-one(1220512-56-0)
• EPA Substance Registry System: (5R,7R)-5,7-bis{[(tert-butyl)(dimethyl)silyl]oxy}-1-(4-hydroxyphenyl)icosan-3-one(1220512-56-0)

Safety Data

• Hazardous Substances Data: 1220512-56-0(Hazardous Substances Data)

Upstream product

• 1220512-55-9 (5R,7R)-1-[4-(benzyloxy)phenyl]-5,7-bis{[(tert-butyl)(dimethyl)silyl]oxy}icos-1-yn-3-one 

Downstream Products

• 945736-74-3 (5R,7R)-5,7-dihydroxy-1-(4-hydroxyphenyl)icosan-3-one 

Relevant articles and documents

The stereoselective total synthesis of aculeatin A and B via prins cyclization

The total synthesis of aculeatins A and B is described proving the versatility of Prins cyclization in natural product synthesis. The approach is convergent and highly stereoselective. Morpholine amide coupling with an alkyne and PIFA-mediated oxidative spirocyclization were utilized as key steps. Georg Thieme Verlag Stuttgart - New York.

Total synthesis of aculeatins A and B from L-malic acid

An efficient total synthesis of the cytotoxic spiroketal natural products aculeatin A and B is described. The synthesis of the 1,3,5-triol moiety with appropriate configuration was accomplished from the commercially available L-malic acid. The key steps in this synthesis are the Barbier allylation, LiAlH4/LiI-mediated syn-stereoselective 1,3-asymmetric reduction, and phenyliodine bis(trifluoroacetate) (=[bis(trifluoroacetoxy)iodo]benzene; PIFA) mediated oxidative spirocyclization.