Concepedia

Glycosidation of glycals by 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) as a catalytic promoter

Kazunobu Toshima, Toru Ishizuka, Goh Matsuo, Masaya Nakata, Mitsuhiro Kinoshita

Journal of the Chemical Society Chemical Communications · 1993 · 78 citations · 5 references

DOI

Concepts

Abstract

O-Glycosidations of glycals 1, 8 and 9 with several alcohols by using a catalytic amount of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) under neutral conditions proceeds smoothly to give the corresponding 2,3-unsaturated glycosides in high yields.

References

5

Specific removal of o-methoxybenzyl protection by DDQ oxidation.

Yuji Oikawa, Tadao Yoshioka, Osamu Yonemitsu · Tetrahedron Letters · 1982 · 614 citations

, , +2

Synthesis of alkyl 4,6-di-o-acetyl-2,3-dideoxy-α-d-threo-hex-2- enopyranosides from 3,4,6-tri-o-acetyl-1,5-anhydro-2-deoxy- d-lyxo-hex-1-enitol (3,4,6-tri-o-acetyl-d-galactal)

Grzegorz Grynkiewicz, Waldemar Priebe, Aleksander Zamojski · Carbohydrate Research · 1979 · 89 citations

, , +2

2,3-Dichloro-5,6-Dicyano-p-Benzoquinone, an efficient, mild, neutral and highly regioselective catalyst for alcoholysis of epoxides

Nasser Iranpoor, I. Mohammadpour Baltork · Tetrahedron Letters · 1990 · 77 citations

, , +5

2,3-Dichloro-5,6-dicyano-<i>p</i>-benzoquinone as a Mild and Efficient Catalyst for the Tetrahydropyranylation of Alcohols

Kiyoshi Tanemura, Takaaki Horaguchi, Tsuneo Suzuki · Bulletin of the Chemical Society of Japan · 1992 · 69 citations

, , +11

Allylic rearrangement of 6-deoxyglycals having practical utility

Prakash M. Bhate, Derek Horton, Waldemar Priebe · Carbohydrate Research · 1985 · 54 citations

, , +2