Efficient Synthesis of Allolactose

Jiang, Rui; Liang, Xiaomei; Shuhui, Jin; Zhang, Jianjun; Wang, Daoquan

doi:10.6023/cjoc201312028

Cited by 4 publications

(4 citation statements)

References 8 publications

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“…However, only syn-addut (1 S ,2 R )- 38 was isolated when 0.3 equiv of K 2 CO 3 was added to the oxidation reaction of 37 at 25 o C. The absolute configurations were determined by comparing the sign and specific rotations of the respective reported molecules (see SI). 65,66,68,69 Optical purities of all dihydroxylated molecules were measured using HPLC/chiral column (SI). To determine the stereochemistry of 49 (which has not been reported previously), we independently prepared (1 S ,2 R ,4 R )- 49 and its (1 R ,2 S ,4 R )-diastereomer by the reaction of ( R )- 48 with OsO 4 (catalytic amount)-NMO followed by silica gel column chromatography (SI).…”

Section: Resultsmentioning

confidence: 99%

Chiral-Substituted Poly-N-vinylpyrrolidinones and Bimetallic Nanoclusters in Catalytic Asymmetric Oxidation Reactions

et al. 2016

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A new class of poly-N-vinylpyrrolidinones containing an asymmetric center at C5 of the pyrrolidinone ring were synthesized from l-amino acids. The polymers, particularly 17, were used to stabilize nanoclusters such as Pd/Au for the catalytic asymmetric oxidations of 1,3- and 1,2-cycloalkanediols and alkenes, and Cu/Au was used for C-H oxidation of cycloalkanes. It was found that the bulkier the C5 substituent in the pyrrolidinone ring, the greater the optical yields produced. Both oxidative kinetic resolution of (±)-1,3- and 1,2-trans-cycloalkanediols and desymmetrization of meso cis-diols took place with 0.15 mol % Pd/Au (3:1)-17 under oxygen atmosphere in water to give excellent chemical and optical yields of (S)-hydroxy ketones. Various alkenes were oxidized with 0.5 mol % Pd/Au (3:1)-17 under 30 psi of oxygen in water to give the dihydroxylated products in >93% ee. Oxidation of (R)-limonene at 25 °C occurred at the C-1,2-cyclic alkene function yielding (1S,2R,4R)-dihydroxylimonene 49 in 92% yield. Importantly, cycloalkanes were oxidized with 1 mol % Cu/Au (3:1)-17 and 30% HO in acetonitrile to afford chiral ketones in very good to excellent chemical and optical yields. Alkene function was not oxidized under the reaction conditions. Mechanisms were proposed for the oxidation reactions, and observed stereo- and regio-chemistry were summarized.

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Section: Resultsmentioning

confidence: 99%

Chiral-Substituted Poly-N-vinylpyrrolidinones and Bimetallic Nanoclusters in Catalytic Asymmetric Oxidation Reactions

et al. 2016

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“…It has been well documented that hetidine-type DAs with a ketone at C-6 and vakognavine-type alkaloids (bearing an aldehyde group at C-19) can transform into their salt form bearing an N , O -acetal in the presence of acids and can return to their free alkaloid form after treatment with bases. 52 Since DAs in plants are mainly extracted by using acids, primarily dilute hydrochloric acid, these quaternary ammonia bases or hetisine salts might be artifact products of the corresponding hetidine-type or vakognavine-type DAs. 53 For example, chemical transformation experiments have suggested that orochrine and 2- O -acetylorochrine are artifacts of the corresponding hetidine-type DAs heterophylloidine and deacetylheterophylloidine, respectively, 54,55 and carmichaelines B–D are indeed the trifluoroacetates of corresponding vakognavine-type C 20 -DAs.…”

Section: Structures and Classificationsmentioning

confidence: 99%

Chemistry and biological activities of hetisine-type diterpenoid alkaloids

Yin

Zhang

et al. 2021

RSC Adv.

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“…The DArk Matter Particle Explore (DAMPE) is a new one in the list, and it's a satellite-borne high energy particle detector supported by the Strategic Pioneer Program on Space Science of the Chinese Academy of Sciences (CAS) [4].…”

Section: Introductionmentioning

confidence: 99%

The plastic scintillator detector for DAMPE

Sun

et al. 2017

Astroparticle Physics

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The DArk Matter Particle Explorer (DAMPE) is a general purposed satelliteborne high energy γ−ray and cosmic ray detector, and among the scientific objectives of DAMPE are the searches for the origin of cosmic rays and an understanding of Dark Matter particles. As one of the four detectors in DAMPE, the Plastic Scintillator Detector (PSD) plays an important role in the particle charge measurement and the photons/electrons separation. The PSD has 82 modules, each consists of a long organic plastic scintillator bar and two PMTs at both ends for readout, in two layers and covers an overall active area larger than 82 cm × 82 cm. It can identify the charge states for relativistic ions from H to Fe, and the detector efficiency for Z=1 particles can reach 0.9999. The PSD has been successfully launched with DAMPE on Dec. 17, 2015. In this paper, the design, the assembly, the qualification tests of the PSD and some of the performance measured on the ground have been described in detail.

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Efficient Synthesis of Allolactose

Cited by 4 publications

References 8 publications

Chiral-Substituted Poly-N-vinylpyrrolidinones and Bimetallic Nanoclusters in Catalytic Asymmetric Oxidation Reactions

Chiral-Substituted Poly-N-vinylpyrrolidinones and Bimetallic Nanoclusters in Catalytic Asymmetric Oxidation Reactions

Chemistry and biological activities of hetisine-type diterpenoid alkaloids

The plastic scintillator detector for DAMPE

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