A Concise, Efficient and Production-Scale Synthesis of a Protected l-Lyxonolactone Derivative:  An Important Aldonolactone Core

A Concise, Efficient and Production-Scale Synthesis of a Protected l-Lyxonolactone Derivative:  An Important Aldonolactone Core

A multikilogram-scale synthesis of l-lyxonolactone-2,3-O-isopropylidene is reported. It proceeds efficiently from an optimized, large-scale, aqueous bromine oxidation of d-ribose to d-ribonolactone including a one-pot isopropylidene formation, and subsequent conversion of the d-ribonolactone-2,3-O-i...

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Veröffentlicht in:Organic process research & development 2006-05, Vol.10 (3), p.484-486
Hauptverfasser: Batra, Hitesh, Moriarty, Robert M, Penmasta, Raju, Sharma, Vijay, Stanciuc, Gabriela, Staszewski, James P, Tuladhar, Sudersan M, Walsh, David A, Datla, Satyanarayana, Krishnaswamy, Sunderraj
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container_end_page 486
container_issue 3
container_start_page 484
container_title Organic process research & development
container_volume 10
creator Batra, Hitesh
Moriarty, Robert M
Penmasta, Raju
Sharma, Vijay
Stanciuc, Gabriela
Staszewski, James P
Tuladhar, Sudersan M
Walsh, David A
Datla, Satyanarayana
Krishnaswamy, Sunderraj
description A multikilogram-scale synthesis of l-lyxonolactone-2,3-O-isopropylidene is reported. It proceeds efficiently from an optimized, large-scale, aqueous bromine oxidation of d-ribose to d-ribonolactone including a one-pot isopropylidene formation, and subsequent conversion of the d-ribonolactone-2,3-O-isopropylidene to l-lyxonolactone-2,3-O-isopropylidene via the derived C5-mesylate and intramolecular relactonization of the product of aqueous potassium hydroxide cleavage of the d-ribonolactone ring. The inversion of configuration at the C4-chiral center is understood in terms of an intermediating C4−C5-epoxide. The overall process is noteworthy for its operational simplicity, stereochemical integrity, and use of inexpensive chemicals.
doi_str_mv 10.1021/op050222n
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title A Concise, Efficient and Production-Scale Synthesis of a Protected l-Lyxonolactone Derivative:  An Important Aldonolactone Core
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