172919-05-0

Basic information

• Product Name: (13R,14R)-4-benzyloxy-13,14-dihydroxy-2,11-dioxatricyclo[13.2.2.1^3,7]eicosa-1⁽¹⁸⁾,3,5,7⁽²⁰⁾,1⁽¹⁹⁾,16-hexaen-10-one
• Synonyms: (13R,14R)-4-benzyloxy-13,14-dihydroxy-2,11-dioxatricyclo[13.2.2.1^3,7]eicosa-1⁽¹⁸⁾,3,5,7⁽²⁰⁾,1⁽¹⁹⁾,16-hexaen-10-one
• CAS NO: 172919-05-0
• Molecular Weight: 420.462
• Mol File: 172919-05-0.mol

Chemical Properties

• CAS DataBase Reference: (13R,14R)-4-benzyloxy-13,14-dihydroxy-2,11-dioxatricyclo[13.2.2.1^3,7]eicosa-1⁽¹⁸⁾,3,5,7⁽²⁰⁾,1⁽¹⁹⁾,16-hexaen-10-one(CAS DataBase Reference)
• NIST Chemistry Reference: (13R,14R)-4-benzyloxy-13,14-dihydroxy-2,11-dioxatricyclo[13.2.2.1^3,7]eicosa-1⁽¹⁸⁾,3,5,7⁽²⁰⁾,1⁽¹⁹⁾,16-hexaen-10-one(172919-05-0)
• EPA Substance Registry System: (13R,14R)-4-benzyloxy-13,14-dihydroxy-2,11-dioxatricyclo[13.2.2.1^3,7]eicosa-1⁽¹⁸⁾,3,5,7⁽²⁰⁾,1⁽¹⁹⁾,16-hexaen-10-one(172919-05-0)

Safety Data

• Hazardous Substances Data: 172919-05-0(Hazardous Substances Data)

Upstream product

• 172919-11-8 (13R,14R)-4-Benzyloxy-13,14-bis-(tert-butyl-dimethyl-silanyloxy)-2,11-dioxa-tricyclo[13.2.2.1^3,7]icosa-1⁽¹⁸⁾,3,5,7⁽²⁰⁾,15⁽¹⁹⁾,16-hexaen-10-one 
• 172919-07-2 2,2-Dimethyl-propionic acid (E)-3-(4-bromo-phenyl)-allyl ester 
• 172919-14-1 ethyl 3-(3'-hydroxy-4'-benzyloxyphenyl)propanoate 
• 172919-08-3 2,2-Dimethyl-propionic acid (E)-3-{4-[2-benzyloxy-5-(2-ethoxycarbonyl-ethyl)-phenoxy]-phenyl}-allyl ester 
• 172919-06-1 2,2-Dimethyl-propionic acid (2R,3R)-3-{4-[2-benzyloxy-5-(2-ethoxycarbonyl-ethyl)-phenoxy]-phenyl}-2,3-dihydroxy-propyl ester 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 100-39-0 benzyl bromide 
• 1122-91-4 4-bromo-benzaldehyde 
• 172919-09-4 2,2-Dimethyl-propionic acid (2R,3R)-3-{4-[2-benzyloxy-5-(2-ethoxycarbonyl-ethyl)-phenoxy]-phenyl}-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-propyl ester 
• 202645-46-3 3-(4-Benzyloxy-3-{4-[(1R,2R)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-phenoxy}-phenyl)-propionic acid 
• 24393-53-1 ethyl (E)-3-(4-bromophenyl)-2-propenoate 
• 4049-39-2 4-benzyloxy-3-hydroxy-benzaldehyde 
• 172919-13-0 2,2-Dimethyl-propionic acid (2R,3R)-3-{4-[2-benzyloxy-5-(2-carboxy-ethyl)-phenoxy]-phenyl}-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-propyl ester 
• 172919-15-2 ethyl 3-(3'-hydroxy-4'-benzyloxyphenyl)-2E-propenoate 

Downstream Products

• 172919-12-9 C₂₅H₂₂O₅ 
• 202645-48-5 combretastatin D-2 benzyl ether 
• 202645-49-6 combretastatin D-1 benzyl ether 
• 126191-23-9 combretastatin D-2 
• 117709-78-1 combretastatin D-1 

Relevant articles and documents

Total synthesis of combretastatins D

The 15-membered caffrane ring of the natural product group of combretastatins D is synthesized in high yield with suitably functionalized saturated seco acids. The key step is a Mitsunobu-type macrolactonization. A common synthon is used for the construct

Total synthesis of natural (-)combretastatin D-1

Combretastatin D-1, (2), was synthesized via a 12 step sequence. Sharpless asymmetric dihydroxylation was used in order to introduce the appropriate asymmetry. Regiospecific cyclodehydration of the diol 3 gave the title compound in 96% ee.