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Synthesis of the tetrasaccharide alpha-D-Glcp(1 -> 3)-alpha-D-Manp-(1 -> 2)-alpha-D-Manp-(1 -> 2)-alpha-D-Manp recognized by calreticulin/calnexin. / Gemma, Emiliano; Lahmann, M.; Oscarson, S.

In: Carbohydrate Research, Vol. 340, No. 16, 21.11.2005, p. 2558-2562.

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TY - JOUR

T1 - Synthesis of the tetrasaccharide alpha-D-Glcp(1 -> 3)-alpha-D-Manp-(1 -> 2)-alpha-D-Manp-(1 -> 2)-alpha-D-Manp recognized by calreticulin/calnexin

AU - Gemma, Emiliano

AU - Lahmann, M.

AU - Oscarson, S.

PY - 2005/11/21

Y1 - 2005/11/21

N2 - The title compound as its methyl glycoside was efficiently synthesized using a block synthesis approach. Halide-assisted glycosidations between 6-O-acetyl-2,3,4-tri-O-benzyl-α-d-glucopyranosyl iodide and ethyl 2-O-acetyl-4,6-di-O-benzyl-1-thio-α-d-mannopyranoside using triphenylphosphine oxide as promoter yielded, with complete α-selectivity, a disaccharide building block in high yield. The perbenzylated derivative of this proved to be an excellent donor affording 88% of the protected target tetrasaccharide in an NIS/AgOTf-promoted coupling to a known methyl dimannoside acceptor. Deprotection through catalytic hydrogenolysis then gave the target compound in 47% overall yield.

AB - The title compound as its methyl glycoside was efficiently synthesized using a block synthesis approach. Halide-assisted glycosidations between 6-O-acetyl-2,3,4-tri-O-benzyl-α-d-glucopyranosyl iodide and ethyl 2-O-acetyl-4,6-di-O-benzyl-1-thio-α-d-mannopyranoside using triphenylphosphine oxide as promoter yielded, with complete α-selectivity, a disaccharide building block in high yield. The perbenzylated derivative of this proved to be an excellent donor affording 88% of the protected target tetrasaccharide in an NIS/AgOTf-promoted coupling to a known methyl dimannoside acceptor. Deprotection through catalytic hydrogenolysis then gave the target compound in 47% overall yield.

KW - Calreticulin substrates

KW - Iodide glycosyl donors

KW - Triphenylphosphine oxide promotion

KW - Thioglycoside block donor

U2 - 10.1016/j.carres.2005.09.001

DO - 10.1016/j.carres.2005.09.001

M3 - Article

VL - 340

SP - 2558

EP - 2562

JO - Carbohydrate Research

T2 - Carbohydrate Research

JF - Carbohydrate Research

SN - 0008-6215

IS - 16

ER -