Stereoselective Synthesis of Diglycosyl Diacylglycerols with Glycosyl Donors Bearing a β-Stereodirecting 2,3-Naphthalenedimethyl Protecting Group

2020 ◽  
Vol 85 (24) ◽  
pp. 16166-16181
Author(s):  
Nahoko Yagami ◽  
Amol M. Vibhute ◽  
Hide-Nori Tanaka ◽  
Naoko Komura ◽  
Akihiro Imamura ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Protecting Group ◽  
Glycosyl Donors

scholarly journals Stereoselective synthesis of glycosides using (salen)Co catalysts as promoters

2015 ◽  
Vol 51 (43) ◽  
pp. 8939-8941 ◽  
Author(s):  
Sandra Medina ◽  
Alexander S. Henderson ◽  
John F. Bower ◽  
M. Carmen Galan
Keyword(s):  
Room Temperature ◽  
Stereoselective Synthesis ◽  
Co Catalysts ◽  
New Class ◽  
Stereoselective Glycosylation ◽  
Glycosyl Donors

The use of (salen)Co catalysts as a new class of bench-stable stereoselective glycosylation promoters of trichloroacetimidate glycosyl donors at room temperature is described.

The Isothiocyanato Moiety: An Ideal Protecting Group for the Stereoselective Synthesis of Sialic Acid Glycosides and Subsequent Diversification

2014 ◽  
Vol 127 (4) ◽  
pp. 1291-1294 ◽  
Author(s):  
Appi Reddy Mandhapati ◽  
Salla Rajender ◽  
Jonathan Shaw ◽  
David Crich
Keyword(s):  
Sialic Acid ◽  
Stereoselective Synthesis ◽  
Protecting Group

Metal-catalyzed Stereoselective and Protecting-group-free Synthesis of 1,2-cis-Glycosides Using 4,6-Dimethoxy-1,3,5-triazin-2-yl Glycosides as Glycosyl Donors

2015 ◽  
Vol 44 (6) ◽  
pp. 846-848 ◽  
Author(s):  
Tomonari Tanaka ◽  
Naoya Kikuta ◽  
Yoshiharu Kimura ◽  
Shin-ichiro Shoda
Keyword(s):  
Protecting Group ◽  
Metal Catalyzed ◽  
Glycosyl Donors

New Effective Synthesis of (N-Acetyl- and N-Stearoyl-2-amino-2-deoxy-β-D-glucopyranosyl)-(1→4)-N-acetylnormuramoyl-L-2-aminobutanoyl-D-isoglutamine, Analogs of GMDP with Immunopotentiating Activity

1998 ◽  
Vol 63 (4) ◽  
pp. 577-589 ◽  
Author(s):  
Miroslav Ledvina ◽  
Daniel Zyka ◽  
Jan Ježek ◽  
Tomáš Trnka ◽  
David Šaman
Keyword(s):  
Protecting Group ◽  
Silver Triflate ◽  
Effective Synthesis ◽  
Methyl Triflate ◽  
Glycosyl Donors

Ethyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (5), prepared by benzylation of ethyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (4), was transformed by reaction with bromine into 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide (6). Thioglycoside 5 in the presence of methyl triflate and glycosylbromide 6 in the presence of silver triflate were used as glycosyl donors for condensation with benzyl 2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside (7), to give benzyl 2-acetamido-3-O-allyl-6-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-2-deoxy-α-D-glucopyranoside (8). Its reductive dephthaloylation with NaBH4/AcOH afforded benzyl 2-acetamido-3-O-allyl-4-O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)- 6-O-benzyl-2-deoxy-α-D-glucopyranoside (11). Compound 11 was N-acylated to give benzyl 2-acetamido-4-O-(2-acylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranosides (12a) or (12b). These compounds were converted into corresponding benzyl 2-acetamido-4-O-(2-acylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-6-O-benzyl-3-O-carboxymethyl-2-deoxy-α-D-glucopyranosides which, by condensation with H-L-Abu-D-isoGln(OBzl) followed by hydrogenolysis of protective benzyl groups, furnished glycopeptides 16a and 16b. Intramolecular O→N migration of the allyl protecting group followed by its reduction to the propyl residue by reaction of compound 8 with hydrazine or hydrazinium acetate, to give benzyl 2-acetamido-4-O-(3,4,6-tri-O-benzyl-2-deoxy-2-propylamino-β-D-glucopyranosyl)-6-O-benzyl-2-deoxy-α-D-glucopyranoside (9), is also described.

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