Enzymes in organic synthesis. 48. Pig liver esterase and porcine pancreatic lipase catalyzed hydrolyses of 3,4-(isopropylidenedioxy)-2,5-tetrahydrofuranyl diesters

Hultin, Philip G.; Mueseler, Franz Josef; Jones, J. Bryan

doi:10.1021/jo00018a033

Cited by 42 publications

(9 citation statements)

References 5 publications

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“…19 Wengel and co-workers 20 reported the first use of esterase catalyzed diastereoselective deacetylation to solve the problem of nucleoside anomer separation. Thus, a lipase-catalyzed deacylation of an anomeric mixture of peracetylated 2'-deoxyribofuranosyl thymines was carried out using two enzymes: wheat germ lipase (WGL) and porcine liver esterase (PLE).…”

Section: Resultsmentioning

confidence: 99%

Scaleable processes for the synthesis of (−)-β-d-2,6-diaminopurine dioxolane (Amdoxovir, DAPD) and (−)-β-d-2-aminopurine dioxolane (APD)

Zhou¹,

Coats²,

Zhang³

et al. 2012

Tetrahedron

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An efficient and scalable synthesis of (−)-DAPD and (−)-APD has been developed. We discovered that t-butyl cyanoacetate can be used as a new additive for the sugar nucleoside base coupling step en route to DAPD with improved β-selectivity and an isolated yield four fold greater than the original process scale method. Using this new process, (−)-DAPD has been prepared on greater than 20 g scale. In the synthesis of (−)-APD, a key enzyme-catalyzed hydrolysis reaction afforded the water-soluble deprotected α-anomer while leaving the β-anomer completely untouched.

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Section: Resultsmentioning

confidence: 99%

Scaleable processes for the synthesis of (−)-β-d-2,6-diaminopurine dioxolane (Amdoxovir, DAPD) and (−)-β-d-2-aminopurine dioxolane (APD)

Zhou¹,

Coats²,

Zhang³

et al. 2012

Tetrahedron

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“…The most likely route to large scale synthesis uses convergent synthesis of a key chiral THF subunit 101 and aryl piperazine amine 102 followed by introduction of the triazole subunit at the end (Scheme 19) [44,46]. After scanning many hydrolases to desymmetrize the diol via selective acylation, hydrolase SP 435 was found to be suitable [47]. After scanning many hydrolases to desymmetrize the diol via selective acylation, hydrolase SP 435 was found to be suitable [47].…”

Section: Posaconaole (Noxafil ® )mentioning

confidence: 99%

Synthetic Approaches to the 2005 New Drugs

Sakya¹,

Jin²,

Liu³

2007

MRMC

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“…We note, however, that the reversal of selectivity in enzyme-mediated hydrolyses, upon substitution of the carbocyclic ring in the substrate, is not without precedent. The selectivity observed in the enzyme-mediated hydrolyses of cyclopentane diacetates has been demonstrated to bear a subtle dependence on the substitution pattern in the five-membered ring. − Thus, while it had not been known at this stage in the synthesis of allosamidin which antipode had in fact been secured, we started with what seemed, superficially, the simplest analogy. The structures drawn at this stage and in schemes thereafter, anticipate later rigorously adduced findings.…”

Section: Allosamizolinementioning

confidence: 99%

The Total Synthesis of Allosamidin. Expansions of the Methodology of Azaglycosylation Pursuant to the Total Synthesis of Allosamidin. A Surprising Enantiotopic Sense for a Lipase-Induced Deacetylation

Griffith

Danishefsky

1996

J. Am. Chem. Soc.

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Allosamidin, recently isolated from mycelial extracts of Streptomyces sp. 1713, is a powerful and selective chitinase inhibitor. The total synthesis of allosamidin is described herein. The electric eel acetylcholinesterase-mediated enantioselective hydrolysis of (trans,trans)-2-(benzyloxy)cyclopentene-1,3-diol diacetate accessed a monoacetyl derivative. Five additional steps produced a protected version of the aglycon (“allosamizoline”) sector of allosamidin. An allal derivative stereoselectively reacted with benzenesulfonamide in the presence of a halonium source to afford a 2β-halo-1α-sulfonamidohexose. Treatment of this product with a strong base generated an intermediate 1,2-sulfonylaziridine, which was trapped with a protected allal derivative to provide a disaccharide glycal. Reiteration of this scheme gave access to the required trisaccharide. Following deprotection, the total synthesis of allosamidin was accomplished. In addition, the method, with modification, gave access to several allosamidin analogs.

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Enzymes in organic synthesis. 48. Pig liver esterase and porcine pancreatic lipase catalyzed hydrolyses of 3,4-(isopropylidenedioxy)-2,5-tetrahydrofuranyl diesters

Cited by 42 publications

References 5 publications

Scaleable processes for the synthesis of (−)-β-d-2,6-diaminopurine dioxolane (Amdoxovir, DAPD) and (−)-β-d-2-aminopurine dioxolane (APD)

Scaleable processes for the synthesis of (−)-β-d-2,6-diaminopurine dioxolane (Amdoxovir, DAPD) and (−)-β-d-2-aminopurine dioxolane (APD)

Synthetic Approaches to the 2005 New Drugs

The Total Synthesis of Allosamidin. Expansions of the Methodology of Azaglycosylation Pursuant to the Total Synthesis of Allosamidin. A Surprising Enantiotopic Sense for a Lipase-Induced Deacetylation

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