cas 133343-34-7, LACTACYSTIN | Articles data

Articles about 133343-34-7Total 19 be found

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A concise route to (+)-lactacystin
A facile chromatography-free route to Kang's intermediate for the synthesis of (+)-lactacystin, a potent proteasome inhibitor, has been developed starting with Brown's asymmetric crotylation of tert-butyl 5-formyl-2,2-dimethyl-1,3- dioxan-5-ylcarbamate, e
Ooi, Hidenori,Ishibashi, Norihisa,Iwabuchi, Yoshiharu,Ishihara, Jun,Hatakeyama, Susumi
p. 7765 - 7768
(2004)
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SYNTHESIS OF (6R,7S)-LACTACYSTIN AND 6-DEOXYLACTACYSTIN FROM A COMMON INTERMEDIATE
The stereocontrolled syntheses of (6R,7S)-lactacystin and deoxylactacystin, analogs of the neurotrophic agent lactacystin, are described.
Corey, E. J.,Reichard, Gregory A.
p. 6973 - 6976
(1993)
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Application of Two Direct C(sp3)-H Functionalizations for Total Synthesis of (+)-Lactacystin
(Figure Presented). Herein, we report a new synthetic route from (S)-pyroglutaminol to (+)-lactacystin, a potent inhibitor of the 20S proteasome. The photoinduced intermolecular C(sp3)-H alkynylation and intramolecular C(sp3)-H acylation chemo- and stereoselectively constructed the tetra- and trisubstituted carbon centers, respectively. The obtained bicycle was transformed into the target compound in a concise manner. The present total synthesis demonstrates the power of the direct C(sp3)-H functionalizations for the assembly of multiple functionalized structures of natural products.
Yoshioka, Shun,Nagatomo, Masanori,Inoue, Masayuki
supporting information
p. 90 - 93
(2015/07/28)

Stereospecific total syntheses of proteasome inhibitors omuralide and lactacystin
Omuralide, a transformation product of the microbial metabolite lactacystin, was the first molecule discovered as a specific inhibitor of the proteasome and is unique in that it specifically inhibits the proteolytic activity of the 20S subunit of the prot
Gu, Wenxin,Silverman, Richard B.
experimental part
p. 8287 - 8293
(2012/04/10)

Enantioselective total syntheses of omuralide, 7-epi-omuralide, and (+)-lactacystin
(Chemical Equation Presented) An alkylidene carbene 1,5-CH insertion has been used as a key step in an enantioselective total syntheses of omuralide, its C7-epimer, and (+)-lactacystin. An additional noteworthy feature of the synthesis is the use of a nov
Hayes, Christopher J.,Sherlock, Alexandra E.,Green, Martin P.,Wilson, Claire,Blake, Alexander J.,Selby, Matthew D.,Prodger, Jeremy C.
p. 2041 - 2051
(2008/09/19)

Catalytic asymmetric total synthesis of (+)-lactacystin
Total synthesis of (+)-lactacystin, a potent and selective proteasome inhibitor, was accomplished using a catalytic enantioselective Strecker reaction of a ketoimine as the initial key step. An enone-derived N-phosphinoyl ketoimine 7 was selected as a sta
Fukuda, Nobuhisa,Sasaki, Kazuki,Sastry,Kanai, Motomu,Shibasaki, Masakatsu
p. 1220 - 1225
(2007/10/03)

α,β-unsaturated β-silyl lmide substrates for catalytic, enantioselective conjugate additions: A total synthesis of (+)-lactacystin and the discovery of a new proteasome inhibitor
Chiral (salen)Al μ-oxo dimer 1 catalyzes the highly enantioselective conjugate addition of carbon-centered nucleophiles to α,β-unsaturated silyl imides. Allyldimethylsilane-substituted imide 4 was identified as an optimal substrate, undergoing addition re
Balskus, Emily P.,Jacobsen, Eric N.
p. 6810 - 6812
(2007/10/03)

Lactacystin analogs
Compounds related to lactacystin and lactacystin Beta-lactone, pharmaceutical compositions containing the compounds, and methods of use.
-
(2008/06/13)

Total synthesis of (+)-lactacystin
A double stereodifferentiating crotylation between aldehyde 1 and silane (S)-2 to afford homoallylic alcohol 3 is the key diastereoselective step (anti:syn > 30:1) in an efficient asymmetric synthesis of (+)-lactacystin. This compound is a metabolite isol
Panek, James S.,Masse, Craig E.
p. 1093 - 1095
(2007/10/03)

An efficient and concise enantioselective total synthesis of lactacystin
A selective, irreversible inhibitor of proteasome function, lactacystin (1) is an important experimental tool in cell biology. An efficient and direct enantioselective synthesis of lactacystin proceeds via the intermediates shown below. This process allow
Corey,Li, Weidong,Nagamitsu, Tohru
p. 1676 - 1679
(2007/10/03)

A new magnesium-catalyzed doubly diastereoselective anti-aldol reaction leads to a highly efficient process for the total synthesis of lactacystin in quantity
A new process is described for metal-catalyzed doubly diastereoselective Mukaiyama aldol coupling of a chiral tertiary α-amino aldehyde and an achiral silyl enol ether to form selectively an anti-aldol product. The metal requirement is strict, since of se
Corey,Li, Weidong,Reichard, Gregory A.
p. 2330 - 2336
(2007/10/03)

Lactacystin analogs
Described herein are compounds related to lactacystin and lactacystin β-lactone, pharmaceutical compositions containing the compounds, and methods of use.
-
(2008/06/13)

Stereoselective total synthesis of (+)-lactacystin from D-glucose
The chiral and stereoselective synthesis of (+)-lactacystin 1, the first non-protein neurotrophic factor having an α,α-disubstituted α- amino acid structure, is described. The highly functionalized γ- lactam portion possessing a tetra-substituted carbon w
Chida, Noritaka,Takeoka, Jun,Ando, Kohji,Tsutsumi, Noriko,Ogawa, Seiichiro
p. 16287 - 16298
(2007/10/03)

Total synthesis of (+)-lactacystin
A total synthesis of the novel neurotrophic agent (+)-lactacystin (1) has been achieved in 11 steps and 14% overall yield from (2R,3S)-3-hydroxyleucine [(+)-16]. The construction and bioassay of several active analogs are also described. A new asymmetric approach furnished the four stereoisomers of 3-hydroxyleucine, as required starting materials in high overall yield and enantiomeric purity.
Nagamitsu, Tohru,Sunazuka, Toshiaki,Tanaka, Haruo,Omura, Satoshi,Sprengeler, Paul A.,Smith III, Amos B.
p. 3584 - 3590
(2007/10/03)

Total Synthesis of (+)-Lactacystin from D-Glucose
The chiral and stereoselective synthesis of (+)-lactacystin 1, the first non-protein neurotrophic factor, is described; the γ-lactam portion possessing a quaternary carbon in 1 was constructed stereoselectively from D-glucose using the allylic trichloroac
Chida, Noritaka,Takeoka, Jun,Tsutsumi, Noriko,Ogawa, Seiichiro
p. 793 - 794
(2007/10/02)

Total synthesis of (+)-lactacystin from (R)-glutamate
-
Uno, Hidemitsu,Baldwin, Jack E.,Russell, Andrew T.
p. 2139 - 2140
(2007/10/02)

An enantioselective synthesis of (6R)-lactacystin
The first enantiospecific, stereocontrolled total synthesis of (6R)-lactacystin, a potential neurotrophic agent, is described.
Corey,Choi, Soongyu
p. 6969 - 6972
(2007/10/02)

Total synthesis of (+)-lactacystin, the first non-protein neurotrophic factor
-
Sunazuka,Nagamitsu,Matsuzaki,Tanaka,Omura,Smith III
p. 5302 - 5302
(2007/10/02)

Total synthesis of lactacystin
-
Corey,Reichard, Gregory A.
p. 10677 - 10678
(2007/10/02)

Chemical Properties

Appearance/Colour :White powder
Melting Point: 233-235 ºC
Boiling Point: 714.875 °C at 760 mmHg
Flash Point:386.143 °C
Density: 1.367 g/cm³
Solubility:Soluble in DMSO (up to 20 mg/ml), in Water (up to 10 mg/ml), or in Ethanol (up to 1 mg/ml).
Storage Temp.:−20°C
Vapor Pressure: 1.31E-23mmHg at 25°C
Refractive Index: 1.559
PKA: 3.11±0.10(Predicted)
PSA: 178.33000
LogP: -0.56230

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133343-34-7

Articles about 133343-34-7Total 19 be found

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Chemical Properties

Appearance/Colour :White powder

Melting Point: 233-235 ºC

Boiling Point: 714.875 °C at 760 mmHg

Flash Point:386.143 °C

Density: 1.367 g/cm³

Solubility:Soluble in DMSO (up to 20 mg/ml), in Water (up to 10 mg/ml), or in Ethanol (up to 1 mg/ml).

Storage Temp.:−20°C

Vapor Pressure: 1.31E-23mmHg at 25°C

Refractive Index: 1.559

PKA: 3.11±0.10(Predicted)

PSA: 178.33000

LogP: -0.56230

Global suppliers and manufacturers of 133343-34-7total 27 suppliers on LookChem

Article Database

133343-34-7

Articles about 133343-34-7Total 19 be found

More Articles about upstream products of 133343-34-7

Chemical Properties

Appearance/Colour :White powder

Melting Point: 233-235 ºC

Boiling Point: 714.875 °C at 760 mmHg

Flash Point:386.143 °C

Density: 1.367 g/cm3

Solubility:Soluble in DMSO (up to 20 mg/ml), in Water (up to 10 mg/ml), or in Ethanol (up to 1 mg/ml).

Storage Temp.:−20°C

Vapor Pressure: 1.31E-23mmHg at 25°C

Refractive Index: 1.559

PKA: 3.11±0.10(Predicted)

PSA: 178.33000

LogP: -0.56230

Global suppliers and manufacturers of 133343-34-7total 27 suppliers on LookChem

Density: 1.367 g/cm³