473543-39-4

Basic information

• Product Name: (1R)-1-((4S,5R)-2,2-dimethyl-5-phenyl-[1,3]-dioxolan-4-yl)-3-buten-1-ol
• Synonyms: (1R)-1-((4S,5R)-2,2-dimethyl-5-phenyl-[1,3]-dioxolan-4-yl)-3-buten-1-ol
• CAS NO: 473543-39-4
• Molecular Weight: 248.322
• Mol File: 473543-39-4.mol

Chemical Properties

• CAS DataBase Reference: (1R)-1-((4S,5R)-2,2-dimethyl-5-phenyl-[1,3]-dioxolan-4-yl)-3-buten-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-1-((4S,5R)-2,2-dimethyl-5-phenyl-[1,3]-dioxolan-4-yl)-3-buten-1-ol(473543-39-4)
• EPA Substance Registry System: (1R)-1-((4S,5R)-2,2-dimethyl-5-phenyl-[1,3]-dioxolan-4-yl)-3-buten-1-ol(473543-39-4)

Safety Data

• Hazardous Substances Data: 473543-39-4(Hazardous Substances Data)

Upstream product

• 77-76-9 2,2-dimethoxy-propane 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 1730-25-2 allylmagnesium bromide 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 7393-43-3 tetraallyl tin 
• 106356-53-0 B-allyldiisopinocampheylborane 
• 622785-65-3 (4R-cis)-5-(2'-formylphenyl)-2,2-dimethyl-1,3-dioxolane-4-carboxaldehyde 
• 473543-36-1 (4S-cis)-5-[2'-(formyl)phenyl]-2,2-dimethyl-1,3-dioxolane-4-methanol acetate 
• 160707-67-5 (4S-cis)-5-[2'-(hydroxymethyl)phenyl]-2,2-dimethyl-1,3-dioxolane-4-methanol 
• 473543-35-0 (4S-cis)-5-[2'-(formyl)phenyl]-2,2-dimethyl-1,3-dioxolane-4-methanol 
• 162600-00-2 ((4S,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl)methanol 
• 473543-37-2 (4S-cis)-5-phenyl-2,2-dimethyl-1,3-dioxolane-4-methanol acetate 
• 130718-77-3 (4R,5R)-cis-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-carbaldehyde 
• 99493-25-1 diisopropyl 2-allyl-1,3,2-dioxaborolane-4,5-dicarboxylate (tartrate allylboronate) 

Downstream Products

• 473543-41-8 (1R)-1-[(4S,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-enyl acrylate 
• 146236-73-9 (+)-goniodiol 
• 163630-06-6 (6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1',3']dioxolan-4'-yl)-5,6-dihydropyran-2-one 
• 474958-85-5 [(1R)-1-((4S,5R)-2,2-dimethyl-5-phenyl-[1,3]-dioxolan-4-yl)-but-3-enyl]-3-phenyl prop-2-enoate 

Relevant articles and documents

Total synthesis and cytotoxicity of (+)- and (-)-goniodiol and 6-epi-goniodiol. Construction of α,β-unsaturated lactones by ring-closing metathesis

(+)-Goniodiol, a potent and selective cytotoxin, and (-)-6-epi-goniodiol, as well as their enantiomers, have been synthesized starting from cinnamyl alcohol. The key steps of the synthesis were Sharpless asymmetric epoxidation and cyclization of an acrylate derivative using ring-closing metathesis reaction. The cytotoxicity of both enantiomers of goniodiol and 6-epi-goniodiol against HL-60 cells was examined.

A total synthesis of the styryllactone (+)-goniodiol from naphthalene

The cytotoxic natural product (+)-goniodiol (1) has been prepared in twelve steps from the enantiomerically pure cis-dihydrocatechol (2), which is readily obtained by microbial oxidation of naphthalene. Elaboration of compound (2) involves an initial oxid

A chemoenzymatic synthesis of the styryllactone (+)-goniodiol from naphthalene

The enantiomerically pure cis-1,2-diol 2, which is obtained by microbial oxidation of naphthalene, has been converted, via a sequence of reactions including oxidative C-C bond cleavage, decarbonylation and ring-closing metathesis steps, into the natural p

Stereoselective syntheses of (+)-goniodiol, (-)-8-epigoniodiol, and (+)-9-deoxygoniopypyrone via alkoxyallylboration and ring-closing metathesis

A convenient synthesis of (+)-goniodiol, (-)-8-epigoniodiol, and (+)-9-deoxygoniopypyrone has been developed via asymmetric alkoxyallylboration and ring-closing metathesis pathways.