Synthesis of 3-S- and 3-Se-glycals by using R-S-S-R and R-Se-Se-R as the nucleophile precursors promoted by Hf(OTf)4 and the temperature-dependent formation of the above-mentioned 3-S- and 3-Se products

Chen, Peiran; Guo, Saisai; Zuo, Junfeng; Chu, Ruiji; He, Xu; Zhu, Guijiang

doi:10.1016/j.tetlet.2020.151648

Cited by 9 publications

(9 citation statements)

References 24 publications

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“…Ahora bien, el funcionamiento real de apegarse se fundamentaba, por parte del titular del huasipungo, en la dimensión demográfica del grupo doméstico ya existente. 26 Esta situación, obviamente, dado el carácter casi fijo del tamaño del lote de tierra en posesión, estaba en correlación con la proporción entre tierras disponibles y cantidad de miembros. Por su parte, las nuevas familias que buscaban apegarse escogían, dentro de la red de parientes posibles, a aquellos titulares en los que efectivamente encontraban las mejores condiciones eco-24.…”

Section: De Forma De Circulación a Estrategia Individual De Reproducciónunclassified

Los Andes: cincuenta años después (1953-2003): homenaje a John Murra

Guerrero¹,

Lechtman²,

Lorandi³

et al. 2003

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Este libro de homenaje a John Murra, antropológo y etnohistoriador de origen rumano, no es solo una muestra del afecto y aprecio con que numerosos colegas y discípulos lo recuerdan, sino, también, un notable conjunto de ensayos que siguen las líneas de investigación abiertas hace ya un poco más de medio siglo por el autor de la tesis que explica la organización social andina en relación con el control vertical de pisos ecológicos. Estos trabajos sistematizan y recuperan la información contenida en las visitas y crónicas coloniales, y la utilizan para ensayar descripciones de acontecimientos históricos fundamentales en la historia peruana, así como para explicar las formas de organización que hasta hoy permanecen en el mundo andino. En este sentido, la publicación que ahora ofrecemos es una muestra palpable de la importancia de las pioneras investigaciones etnohistóricas de John Murray de la profunda huella que sus trabajos han dejado en los estudios andinos.

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Section: De Forma De Circulación a Estrategia Individual De Reproducciónunclassified

Los Andes: cincuenta años después (1953-2003): homenaje a John Murra

Guerrero¹,

Lechtman²,

Lorandi³

et al. 2003

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“…The products were obtained in mixtures of 1-thio-sugars with α-form as the major selectivity, but β-1-thiosugar was quite challenging to gain . Sometimes 3-thiosugars were also found during the Ferrier reaction study but the yield, stereoselectivity, and regioselectivity were not so satisfactory . In continuation of our long-held interest in the exploration of highly reactive 3,4- O -carbonate-glycal donors and inspired by linear/branched allylation catalyzed by different metals, herein, we reported the first catalyst-regulated regioselectivity of thiosugar synthesis from glycals (Scheme c).…”

mentioning

confidence: 92%

Catalyst-Controlled Regiodivergent Synthesis of 1- and 3-Thiosugars with High Stereoselectivity and Chemoselectivity

Yue-xin

Jiao

et al. 2021

ACS Catal.

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An effective regiodivergent synthesis toward 1-and 3thiosugars was achieved through palladium and cobalt catalysis, respectively. β-1-Thiosugars were obtained from 3,4-O-carbonateglycals and various thiols catalyzed by Pd 2 (dba) 3 in good yields with exclusive stereoselectivity and chemoselectivity, while only (3S)-3thiosugars were generated via Co(BF 4 ) 2 . Experiments and DFT calculations supported the proposed mechanism that the thiol moiety preferred to form a hydrogen bond with C4-oxygen from top-face in Pd conditions but thiols would coordinate with cobalt from bottom-face in Co conditions. The difference between Pd/Co−C1 and Pd/Co−C3 bond lengths of key intermediates provided further insights into the 1,3-regioselectivity.

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“…In another report, Zhu's reported Lewis acid catalyzed synthesis of 3-thiosugar which requires harsh condition and the formation of mixtures of the product along with 1-thiosugar as a side product. [11] Moreover, Mangione and Spanevello's group reported the multiple-step synthesis of 3-thiomannoside derivative from levoglucosenone which involves a series of multiple steps to obtain only 3thiomannoside derivatives. [12] From our previous work, we reported 2-ketoglycal in the presence of Lewis acid, soft nucleophiles like thiophenol prefers to attack at the C3 position of glycals.…”

Section: Introductionmentioning

confidence: 99%

2‐Ketophenyl Assisted Biomimetic Synthesis of 3‐Thio Substituted Glycals at Room Temperature

Zargar,

Sakander,

Mukherjee

2023

Eur J Org Chem

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Herein we designed a strategy for the synthesis of regioselective and stereoselective displacement of C‐3 acetate group in the presence of other C‐4 and C‐6 acetate of 2‐ketophenyl‐glycal by different aromatic and cyclic aliphatic thiol nucleophiles taking inspiration from cytosolic esterase mediated thiolation of glucosamine sugars into cellular glycan. Under a mild base condition at room temperature, the protocol generated a library of 3‐arylthiosugars with excellent yields and high axial selectivity. This stereoselective approach tolerated well with different ester‐protected glycals and thiophenols, aliphatic cyclic thiols, and mercaptans. A variety of control experiments were conducted to establish the mechanism and reason behind the stereoselectivity.

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Synthesis of 3-S- and 3-Se-glycals by using R-S-S-R and R-Se-Se-R as the nucleophile precursors promoted by Hf(OTf)4 and the temperature-dependent formation of the above-mentioned 3-S- and 3-Se products

Cited by 9 publications

References 24 publications

Los Andes: cincuenta años después (1953-2003): homenaje a John Murra

Los Andes: cincuenta años después (1953-2003): homenaje a John Murra

Catalyst-Controlled Regiodivergent Synthesis of 1- and 3-Thiosugars with High Stereoselectivity and Chemoselectivity

2‐Ketophenyl Assisted Biomimetic Synthesis of 3‐Thio Substituted Glycals at Room Temperature

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