The use of 2,6-anhydro-2-thio sugar for a highly stereocontrolled glycosylation: A novel strategy for synthesis of 2,6-dideoxy-α-glycosides

Toshima, Kazunobu; Mukaiyama, Satsuki; Ishiyama, Takashi; Tatsuta, Kuniaki

doi:10.1016/s0040-4039(00)89059-0

Cited by 28 publications

(11 citation statements)

References 12 publications

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“…Thus, in additions of O nucleophiles to 2-oxyfuranosyl oxonium ions, the 2-oxy groups are syn directing. , It should be added that it is also true for N nucleophiles …”

Section: 52 Stereochemical Evidence: Azaallyl and Oxaalkyl Stereogen...mentioning

confidence: 99%

Inductive and Resonance Effects of Substituents on π-Face Selection

Cieplak

1999

Chem. Rev.

144

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“…Thus, in additions of O nucleophiles to 2-oxyfuranosyl oxonium ions, the 2-oxy groups are syn directing. , It should be added that it is also true for N nucleophiles …”

Section: 52 Stereochemical Evidence: Azaallyl and Oxaalkyl Stereogen...mentioning

confidence: 99%

Inductive and Resonance Effects of Substituents on π-Face Selection

Cieplak

1999

Chem. Rev.

144

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“…The 2-thioglycosides obtained (Tables 1 and 2) were excellent intermediates, after removal of the sulfur atom, for the synthesis of the corresponding aryl 2-deoxy-O-glycosides. [16] In fact, treatment of cycloadducts 4 a, 17, and 24 with Raney nickel [17] in wet THF at room temperature afforded the corresponding 2-deoxy-a-or 2-deoxy-b-O-glycosides 39, 40, 41 in good yield and without any undesired rearrangement, which usually occurs when acidic conditions are used [18,19] (Scheme 5).…”

Section: Synthesis Of Aryl 2-deoxy-o-glycosidesmentioning

confidence: 99%

ortho-Thioquinones, New Acceptors for the Stereoselective Synthesis of Aryl 2-Deoxy-O-Glycosides

et al. 1999

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Abstract:a-Hydroxynaphthylthiophthalimide (1) is a suitable precursor of the reactive ortho-thioquinone 2, which can be generated in situ and trapped by glycals. The reaction is an inverse electron-demand [42] cycloaddition that occurs in a totally regioselective and highly stereoselective way. A series of differently substituted glycals (3, 5 ± 12, 21, 22, 38) as well as various ortho-thioquinones (25 ± 27) are successfully used as electron-rich dienophiles and electron-poor dienes, respectively, with chloroform, dimethylformamide, and dimethyl sulfoxide as solvents. The stereochemistry of substituents on the dienophile strongly influences the selectivity of the cycloaddition, which becomes totally stereoselective when galactals 8 ± 10 or arabinals 21 and 22 are employed as dienophiles. Among the heterodienes tested, the a-naphthol derivative 25 and the tyrosine derivative 26 were successfully used to prepare the naphthyl-a-O-rhamnoside 32 a and the tyrosine-a-O-glucoside 34, respectively. Cycloadducts 4 a, 17, 24, and 33 a were successfully desulfurized, affording the corresponding aryl 2-deoxy-a-O-glycosides 39 and 40 ± 42.

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“…[80][81][82][83][84][85][86] Both glycosylations of the 2,6-anhydro-2thio sugars possessing a phenylthio group 142 with NBS and 2,6-anhydro-2-thio fluoride 143 with several Lewis acids provided 2,6-anhydro-2-thio-a-glycoside a-145 in high yields with a nearly complete selectivity. [80][81][82][83][84][85][86] Both glycosylations of the 2,6-anhydro-2thio sugars possessing a phenylthio group 142 with NBS and 2,6-anhydro-2-thio fluoride 143 with several Lewis acids provided 2,6-anhydro-2-thio-a-glycoside a-145 in high yields with a nearly complete selectivity.…”

Section: Indirect Synthetic Methodsmentioning

confidence: 99%