89616-54-6

Basic information

• Product Name: (R)-1-Phenyl-1-((2S,4aR,7R,8aS)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-propan-1-ol
• Synonyms: (R)-1-Phenyl-1-((2S,4aR,7R,8aS)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-propan-1-ol
• CAS NO: 89616-54-6
• Molecular Weight: 334.523
• Mol File: 89616-54-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (R)-1-Phenyl-1-((2S,4aR,7R,8aS)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-propan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-Phenyl-1-((2S,4aR,7R,8aS)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-propan-1-ol(89616-54-6)
• EPA Substance Registry System: (R)-1-Phenyl-1-((2S,4aR,7R,8aS)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-propan-1-ol(89616-54-6)

Safety Data

• Hazardous Substances Data: 89616-54-6(Hazardous Substances Data)

Upstream product

• 925-90-6 ethylmagnesium bromide 
• 89616-56-8 Phenyl-((2S,4aR,7R,8aS)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-methanone 
• 59324-06-0 hexahydro-4,7,7-trimethyl-4H-benzoxathiane 
• 100-52-7 benzaldehyde 

Downstream Products

• 89616-49-9 (R)-2-hydroxy-2-phenyl-butyric acid methyl ester 
• 24256-91-5 (S)-2-hydroxy-2-phenylbutanoic acid 
• 3966-31-2 (R)-2-hydroxy-2-phenylbutyric acid 
• 21504-01-8 (R)-2-hydroxy-2-phenylbutanal 

Relevant articles and documents

Asymmetric Syntheses Based on 1,3-Oxathianes. 2. Synthesis of Chiral Tertiary α-Hydroxy Aldehydes, α-Hydroxy Acids, Glycols (RR'C(OH)CH2OH), and Carbinols (RR'C(OH)CH3) in High Enantiomeric Purity

A chiral 1,3-oxathiane (5) prepared from (+)-pulegone in three steps is converted to diastereomerically pure equatorial 2-acyl derivatives by lithiation, condensation with aldehydes, and Me2SO oxidation.Reaction of the resulting ketones with Grignard reagents at -78 deg C again proceeds highly stereoselectively (diastereomer excess generally above 90percent) according to Cram's rule (cyclic model).The resulting tertiary carbinols when cleaved with NCS/AgNO3 give chiral tertiary α-hydroxy aldehydes, RR'C(OH)CHO, plus a mixture of epimeric sultines which may be readily reconverted to the starting oxathiane.The hydroxy aldehydes have been oxidized to chiral tertiary α-hydroxy acids, RR'C(OH)CO2H, and reduced to primary-tertiary glycols, RR'C(OH)CH2OH, and further to tertiary carbinols, RR'C(OH)CH3, all with over 90percent ee.The opposite enantiomers of these compounds (again >90percent ee) may be obtained by starting with a diastereomeric 1,3-oxathiane (6), also available from (+)-pulegone.The configurations of the chiral products may be deduced from the manner of preparation and the assumption that Cram's rule is valid and agree with prior assignments in the literature.