Samarium Diiodide Mediated Coupling of Glycosyl Phosphates with Carbon Radical or Anion Acceptors—Synthesis of C‐Glycosides

Hung, Shang‐Cheng; Wong, Chi‐Huey

doi:10.1002/anie.199626711

Cited by 63 publications

(18 citation statements)

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“…Taken together with another weak correlation observed between H-1Ј and H-4Ј, this established that the minor isomer was indeed 5β and was of (1ЈR) configuration. These results are in contrast with a closely related example in the literature, [17] in which the SmI 2 -mediated coupling of tri-O-benzyl-d-ribofuranoside 1-phosphate with cyclopentanone gave the product of (1ЈR) configuration as the major one. Examination of the NMR spectroscopic data for this example show a much better agreement with the data for 5β than with those for 5α, thus indicating that the correct assignment of stereochemistry seems to have been made in the literature example.…”

Section: Resultscontrasting

confidence: 99%

Samarium Diiodide Mediated Coupling of 2‐Pyridylsulfonyl Furanosides with Aldehydes and Ketones: A General Synthesis of C‐Furanosides

2015

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Diiodosamarium‐mediated coupling of anomeric 2‐pyridyl sulfones derived from furanosides with carbonyl compounds, aldehydes, and ketones gave α‐hydroxylated 2,5‐trans‐dialkylated tetrahydrofurans with good yields and useful stereoselectivities. The main control element of the reaction is the substituent on the 4‐position or the starting furanosyl sulfone. C‐Furanosides of D‐arabinose and of D‐ribose were obtained from sulfones prepared from the corresponding furanosides. Finally, a di‐C‐arabinofuranoside, a C‐disaccharide analogue of a major motif of the arabinogalactan from the mycobacterial cell wall, was prepared.

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Section: Resultscontrasting

confidence: 99%

Samarium Diiodide Mediated Coupling of 2‐Pyridylsulfonyl Furanosides with Aldehydes and Ketones: A General Synthesis of C‐Furanosides

2015

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“…Mannosyl phosphates also generate radical species in the presence of SmI 2 [5,174]. These radicals smoothly add to ketones and aldehydes (Table 23).…”

Section: [ ( S C H E M E _ 3 6 ) T D $ F I G ]mentioning

confidence: 99%

The synthesis of d-C-mannopyranosides

Choumane¹,

Banchet²,

Probst³

et al. 2010

Comptes Rendus. Chimie

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“…An early example of this methodology is the formation of bicyclic dideoxy sugars by intramolecular radical cyclization after Giese. 93 De Mesmaeker et al ., 94 Hung and Wong, 54 Sinay¨, 50 and Czernecki et al . 95 took advantage of this protocol for the synthesis of different cyclic C-glycosides 80-82 (Scheme 9).…”

Section: Synthesis Of C-glycosidesmentioning

confidence: 99%

“…51,52 acceptor in the initial electron-transfer reaction and subsequent addition to aldehyde 55 to give the α-d-Manp-(1 → 6a)-6a-carba-α-d-Glcp derivative 56 has been proposed by Hung and Wong. 54 C-Disaccharides with the four possible linkages (1 → 2a), (1 → 3a), (1 → 4a), and (1 → 6a) have been prepared using this methodology, and the structures and yields are summarized in Table 1 (Entries 1-12). Of special interest are the samariation of d-GlcpNAc which gave a C-disaccharide with an anomalous 1,2-cis disposition preferentially, attributable to strong complexation between the Nacetamido group and the samarium ion (Entry 6), the Ni(II)-catalyzed reactions (Entries 7-10), and the synthesis of a C-trisaccharide in a single step from a 3,6-diformylmanno derivative (Entry 11).…”

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confidence: 99%