91603-58-6

Basic information

• Product Name: (2R,4R,5R)-6-benzyloxy-4,5-isopropylidenedioxy-2-hexanol
• CAS NO: 91603-58-6
• Molecular Weight: 280.364
• Mol File: 91603-58-6.mol

Chemical Properties

• CAS DataBase Reference: (2R,4R,5R)-6-benzyloxy-4,5-isopropylidenedioxy-2-hexanol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4R,5R)-6-benzyloxy-4,5-isopropylidenedioxy-2-hexanol(91603-58-6)
• EPA Substance Registry System: (2R,4R,5R)-6-benzyloxy-4,5-isopropylidenedioxy-2-hexanol(91603-58-6)

Safety Data

• Hazardous Substances Data: 91603-58-6(Hazardous Substances Data)

Upstream product

• 91526-99-7 1-((4R,5R)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propane-2-one 

Downstream Products

• 91527-01-4 (R,R,R)-5-acetoxy-1-benzyloxy-2,3-(isopropylidenedioxy)hexane 
• 21142-67-6 colletodiol 
• 91526-96-4 E-(4R,5R,7R)-trihydroxy-2-octenoic acid 

Relevant articles and documents

(+)-COLLETODIOL SYNTHESIS FROM (S,S)-TARTARIC ACID AND (R)-HYDROXY-BUTYRIC ACID

E-(R)-5-Hydroxy-2-hexenoic acid (4) and the acetonide of E-(4R,5R,7R)-trihydroxy-2-octenoic acid (3) are joined to give, after deprotection, (+)-colletodiol (1).The syntheses of the two hydroxy-acids from poly-(R)-3-hydroxy-butenoate (PHB) and (-)-tartaric acid, respectively, are outlined.

Total synthesis of (+)-colletodiol from (S,S)-tartrate and (R)-3-hydroxybutanoate

The macrodiolide antibiotic (+)-colletodiol (7, Scheme 1) was synthesised.The configuration was thus proven to be (6R,11R,12R,14R). - Key intermediates (Schemes 9 and 10) are the two hydroxy acids 43 and 64, which were prepared from dimethyl (S,S)-tartrate in 20percent overall yield (12 steps) and from (R)-3-hydroxybutanoate in 57percent overall yield (6 steps), respectively.The two hydroxy acids were cyclised to give, after deprotection, the title compound. - Our investigations led to the production of a large number of chiral building blocks, many of them in different stereoisomeric forms.