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54702-04-4

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54702-04-4 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 54702-04-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,4,7,0 and 2 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 54702-04:
(7*5)+(6*4)+(5*7)+(4*0)+(3*2)+(2*0)+(1*4)=104
104 % 10 = 4
So 54702-04-4 is a valid CAS Registry Number.

54702-04-4Relevant articles and documents

Total synthesis of (-)-exiguolide via an organosilane-based strategy

Li, Hongze,Xie, Hengmu,Zhang, Zhigao,Xu, Yongjin,Lu, Ji,Gao, Lu,Song, Zhenlei

, p. 8484 - 8487 (2015)

An organosilane-based strategy has been used to accomplish the convergent total synthesis of (-)-exiguolide. The key steps involve: (1) geminal bis(silyl) Prins cyclization to construct the A ring; (2) silicon-protected RCM reaction to construct the 20-me

Total Synthesis of (-)-Exiguolide

Zhang, Zhigao,Xie, Hengmu,Li, Hongze,Gao, Lu,Song, Zhenlei

, p. 4706 - 4709 (2015)

A concise total synthesis of (-)-exiguolide has been completed in an overall 2.8% yield over 20 steps in the longest linear path. The key strategies involve (1) Prins cyclization/homobromination of dienyl alcohol with the B ring-substituted aldehyde, prep

Silacycles as templates for acyclic diastereoselection

Soderquist, John A.,Negron, Alvin

, p. 9397 - 9400 (1998)

The 4-substituted silacyclohex-3-enes (3) prepared from the vinyl triflate (9) derived from 1,1-dimethyl-1-silacyclohexan-4-one (1) and higher- order organocuprates provides a versatile template for the construction of non-racemic 3-methyl-4-penten-1-ol (6). Through asymmetric hydroboration, 3 affords the requisite β-hydroxysilane (4) with the idea/geometry to undergo elimination to the chiral acyclic silane (5) which is oxidatively converted to 6.

Synthesis of 10-Aza-9-oxakalkitoxin by N-O Bond Formation

Crich, David,Upadhyaya, Kapil

supporting information, p. 1833 - 1836 (2022/03/16)

We describe a formal synthesis of 10-aza-9-oxakalkitoxin, the hydroxalog of the cytotoxic marine natural product kalkitoxin, that features Mukaiyama Markovnikov silyl peroxidation of a terminal alkene and N-O bond formation as the central enabling steps.

Pd(II)-Catalyzed [4 + 2] Heterocyclization Sequence for Polyheterocycle Generation

Glaisyer, Elizabeth L.,Watt, Michael S.,Booker-Milburn, Kevin I.

supporting information, p. 5877 - 5880 (2018/09/25)

A new Pd(II)-catalyzed cascade sequence for the formation of polyheterocycles, from simple starting materials, is reported. The sequence is applicable to both indole and pyrrole substrates, and a range of substituents are tolerated. The reaction is thought to proceed by a Pd(II)-catalyzed C-H activated Heck reaction followed by a second Pd(II)-catalyzed aza-Wacker reaction with two Cu(II)-mediated Pd(0) turnovers per sequence. The sequence can be considered a formal [4 + 2] heterocyclization.

Br?nsted Acid Catalysis in Visible-Light-Induced [2+2] Photocycloaddition Reactions of Enone Dithianes

Brenninger, Christoph,P?thig, Alexander,Bach, Thorsten

supporting information, p. 4337 - 4341 (2017/04/04)

1,3-Dithiane-protected enones (enone dithianes) were found to undergo an intramolecular [2+2] photocycloaddition under visible-light irradiation (λ=405 nm) in the presence of a Br?nsted acid (7.5–10 mol %). Key to the success of the reaction is presumably the formation of colored thionium ions, which are intermediates of the catalytic cycle. Cyclobutanes were thus obtained in very good yields (78–90 %). It is also shown that the dithiane moiety can be reductively or oxidatively removed without affecting the photochemically constructed ring skeleton.

COMPOUNDS THAT INHIBIT MCL-1 PROTEIN

-

Page/Page column 1196; 1197, (2017/09/15)

Provided herein are myeloid cell leukemia 1 protein (Mcl-1) inhibitors, methods of their preparation, related pharmaceutical compositions, and methods of using the same. For example, provided herein are compounds of Formula I, and pharmaceutically acceptable salts thereof and pharmaceutical compositions containing the compounds. The compounds and compositions provided herein may be used, for example, in the treatment of diseases or conditions, such as cancer.

Total Synthesis of Unsymmetrically Oxidized Nuphar Thioalkaloids via Copper-Catalyzed Thiolane Assembly

Lacharity, Jacob J.,Fournier, Jeremy,Lu, Ping,Mailyan, Artur K.,Herrmann, Aaron T.,Zakarian, Armen

, p. 13272 - 13275 (2017/10/05)

An asymmetric total synthesis of (+)-6-hydroxythiobinupharidine (1b) and (-)-6-hydroxythionuphlutine (2b), a set of hemiaminal containing dimeric sesquiterpenes isolated from yellow water lilies of the Nuphar genus, is described. The central bis-spirocyclic tetrahydrothiophene ring was forged through the Stevens rearrangement of a sulfonium ylide, generated in situ from the coupling of a copper-carbene with a spirocyclic thietane. This strategy diverges both from the proposed biosynthesis1 and previous syntheses of this family of alkaloids,2,3 all of which employ dimerization of symmetric monomers to form the aforementioned thiaspirane. The coupling of unsymmetrical monomers allowed access to the unsymmetrically oxidized product 2b for the first time.

Molecular basis for the enantio-and diastereoselectivity of burkholderia cepacia lipase toward γ-butyrolactone primary alcohols

Eum, Heesung,Kazlauskas, Romas J.,Ha, Hyun-Joon

, p. 3585 - 3599 (2015/02/19)

Burkholderia cepacia lipase (BCL) shows high enantioselectivity toward chiral primary alcohols, but this enantioselectivity is often unpredictable, especially for substrates that contain an oxygen at the stereocenter. For example, BCL resolves bsubstituted-g-acetyloxymethyl-g-butyrolactones (acetates of a chiral primary alcohol) by hydrolysis of the acetate, but the enantioselectivity varies with the nature and orientation of the b-alkyl substituent. BCL favors the (R)-primary alcohol when the balkyl substituent is hydrogen (E=30) or trans methyl (E=38), but the (S)-primary alcohol when it is cis methyl (E=145). To rationalize this unusual selectivity, we used a combination of experiments to show the importance of polar interactions and modeling to reveal differences in orientations of the enantiomers. Removal of either the lactone carbonyl in the substrate or the polar side chains in the enzyme by using a related enzyme without these side chains decreased the enantioselectivity at least four-fold. Modeling revealed that the slow enantiomers do not bind by exchanging the location of two substituents relative to the fast enantiomer. Instead, three substituents remain in the same region, but the fourth substituent, hydrogen, inverts to a new location, like an umbrella in a strong wind. In this orientation the favored stereoisomers have similar shapes, thus accounting for the unusual stereoselectivity. The ratio of catalytically productive orientations for the fast vs. slow enantiomers in a molecular dynamic simulation correlated (R2=0.82) with the degree of enantioselectivity including the case where the enantioselectivity reversed. Weighting this ratio by the ratio of Hbonds in the polar interaction to account for different binding strengths improved the correlation with the measured enantioselectivity to R2=0.97. The modeling identifies key interactions responsible for high enantioselectivity in this class of substrates.

Molecular basis for the enantio- and diastereoselectivity of burkholderia cepacia lipase toward γ-Butyrolactone primary alcohols

Eum, Heesung,Kazlauskas, Romas J.,Ha, Hyun-Joon

, p. 3585 - 3599 (2015/02/19)

Burkholderia cepacia lipase (BCL) shows high enantioselectivity toward chiral primary alcohols, but this enantioselectivity is often unpredictable, especially for substrates that contain an oxygen at the stereocenter. For example, BCL resolves bsubstituted- g-acetyloxymethyl-g-butyrolactones (acetates of a chiral primary alcohol) by hydrolysis of the acetate, but the enantioselectivity varies with the nature and orientation of the b-alkyl substituent. BCL favors the (R)-primary alcohol when the balkyl substituent is hydrogen (E=30) or trans methyl (E=38), but the (S)-primary alcohol when it is cis methyl (E=145). To rationalize this unusual selectivity, we used a combination of experiments to show the importance of polar interactions and modeling to reveal differences in orientations of the enantiomers. Removal of either the lactone carbonyl in the substrate or the polar side chains in the enzyme by using a related enzyme without these side chains decreased the enantioselectivity at least four-fold. Modeling revealed that the slow enantiomers do not bind by exchanging the location of two substituents relative to the fast enantiomer. Instead, three substituents remain in the same region, but the fourth substituent, hydrogen, inverts to a new location, like an umbrella in a strong wind. In this orientation the favored stereoisomers have similar shapes, thus accounting for the unusual stereoselectivity. The ratio of catalytically productive orientations for the fast vs. slow enantiomers in a molecular dynamic simulation correlated (R2=0.82) with the degree of enantioselectivity including the case where the enantioselectivity reversed. Weighting this ratio by the ratio of Hbonds in the polar interaction to account for different binding strengths improved the correlation with the measured enantioselectivity to R2=0.97. The modeling identifies key interactions responsible for high enantioselectivity in this class of substrates.

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