838906-52-8

Basic information

• Product Name: Pentanedioic acid, 3-(phenylmethoxy)-, diethyl ester
• CAS NO: 838906-52-8
• Molecular Formula: C16H22O5
• Molecular Weight: 294.348
• Mol File: 838906-52-8.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Pentanedioic acid, 3-(phenylmethoxy)-, diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Pentanedioic acid, 3-(phenylmethoxy)-, diethyl ester(838906-52-8)
• EPA Substance Registry System: Pentanedioic acid, 3-(phenylmethoxy)-, diethyl ester(838906-52-8)

Safety Data

• Hazardous Substances Data: 838906-52-8(Hazardous Substances Data)

Upstream product

• 91424-41-8 diethyl 3-<(trimethylsilyl)oxy>pentanedioate 
• 100-52-7 benzaldehyde 
• 32328-03-3 diethyl 3-hydroxyglutarate 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 100-39-0 benzyl bromide 

Downstream Products

• 259263-49-5 3-(benzyloxy)pentane-1,5-diol 
• 1607830-40-9 (S)-3-(benzyloxy)-4-(benzyloxycarbonylamino)butyric acid 
• 1443774-76-2 (R)-methyl 3-(benzyloxy)-6-cyano-5-oxohexanoate 
• 1443774-74-0 (5R)-dimethyl 5-(benzyloxy)-2-cyano-3-oxoheptanedioate 
• 112904-69-5 (R)-3-(benzyloxy)-5-methoxy-5-oxopentanoic acid 
• 117365-69-2 (S)-3-(benzyloxy)-5-methoxy-5-oxopentanoic acid 
• 791115-50-9 methyl 2-((4R,6R)-6-(cyanomethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate 
• 1574495-27-4 methyl 2-((4R,6S)-6-(cyanomethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate 

Relevant articles and documents

Oxonium ylide rearrangement of enzymatically desymmetrized glutarates

The combination of an enzyme-mediated enantioselective desymmetrization of readily available 3-benzyloxyglutarates and subsequent rhodium-catalyzed oxonium ylide rearrangement of their corresponding in situ derived diazo ketones offers a very concise and highly stereoselective access to functionalized tetrahydrofuranone building blocks.

Kirmse–Doyle- and Stevens-Type Rearrangements of Glutarate-Derived Oxonium Ylides

A novel chemoenzymatic synthetic cascade enables the preparation of densely decorated tetrahydrofuran building blocks. Here, the lipase-catalyzed desymmetrization of 3-alkoxyglutarates renders highly enantioenriched carboxylic acid intermediates, whose subsequent activation and oxonium ylide rearrangement by means of rhodium or copper complexes furnishes functionalized O-heterocycles with excellent diastereoselectivity. The two-step protocol offers a streamlined and flexible synthesis of tetrahydrofuranones bearing different benzylic, allylic or allenylic side chains with full control over multiple stereogenic centers.

Synthesis of GABOB and GABOB-Based Chiral Units Possessing Distinct Protecting Groups

In addition to the varied biological activity of GABOB (4-amino-3-hydroxybutanoic acid), the structure of its protected derivatives makes them interesting chiral intermediates for the synthesis of more complex compounds. A stereoselective route to GABOB derivatives with three different protecting groups is presented, using anhydride desymmetrization as a chirality-inducing step. Selective removal of the protecting groups gave compounds with a free carboxylic acid or hydroxy group. Removal of all of the protecting groups allowed GABOB to be isolated in good yield and with excellent ee.