Convenient synthesis of an N-glycan octasaccharide of the bisecting type

Guangfa Wang; Wei Zhang; Zhichao Lu; Peng Wang; Xiuli Zhang; Yingxia Li

doi:10.1021/jo900016j

Convenient synthesis of an N-glycan octasaccharide of the bisecting type

Guangfa Wang, Wei Zhang, Zhichao Lu, Peng Wang, Xiuli Zhang, Yingxia Li

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Abstract

Convenient synthesis of an N-glycan octasaccharide (A) of the bisecting type was described. The stable and easily prepared orthoester F, 3 -O-chloroacetyl-4 ,6 -O-benzylidene-α-D-glucopyranose 1, 2 (chloromethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-3, 6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosylazide-4 -yl orthoacetate), was designed as the key intermediate with two advantages: (1) distinguishing OH-2 from OH-3 in β-D-glucopyranoside to construct the central β-D-mannopyranoside by inverting the configuration of OH-2 in β-D-glucopyranoside and (2) distinguishing OH-4 and OH-6 from OH-3 in the β-D-mannopyranoside to introduce the bisecting GlcNAc residue.

Original language	English
Pages (from-to)	2508-2515
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	74
Issue number	6
DOIs	https://doi.org/10.1021/jo900016j
State	Published - 20 Mar 2009
Externally published	Yes

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title = "Convenient synthesis of an N-glycan octasaccharide of the bisecting type",

abstract = "Convenient synthesis of an N-glycan octasaccharide (A) of the bisecting type was described. The stable and easily prepared orthoester F, 3 -O-chloroacetyl-4 ,6 -O-benzylidene-α-D-glucopyranose 1, 2 (chloromethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-3, 6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosylazide-4 -yl orthoacetate), was designed as the key intermediate with two advantages: (1) distinguishing OH-2 from OH-3 in β-D-glucopyranoside to construct the central β-D-mannopyranoside by inverting the configuration of OH-2 in β-D-glucopyranoside and (2) distinguishing OH-4 and OH-6 from OH-3 in the β-D-mannopyranoside to introduce the bisecting GlcNAc residue.",

author = "Guangfa Wang and Wei Zhang and Zhichao Lu and Peng Wang and Xiuli Zhang and Yingxia Li",

year = "2009",

month = mar,

day = "20",

doi = "10.1021/jo900016j",

language = "English",

volume = "74",

pages = "2508--2515",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "6",

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TY - JOUR

T1 - Convenient synthesis of an N-glycan octasaccharide of the bisecting type

AU - Wang, Guangfa

AU - Zhang, Wei

AU - Lu, Zhichao

AU - Wang, Peng

AU - Zhang, Xiuli

AU - Li, Yingxia

PY - 2009/3/20

Y1 - 2009/3/20

N2 - Convenient synthesis of an N-glycan octasaccharide (A) of the bisecting type was described. The stable and easily prepared orthoester F, 3 -O-chloroacetyl-4 ,6 -O-benzylidene-α-D-glucopyranose 1, 2 (chloromethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-3, 6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosylazide-4 -yl orthoacetate), was designed as the key intermediate with two advantages: (1) distinguishing OH-2 from OH-3 in β-D-glucopyranoside to construct the central β-D-mannopyranoside by inverting the configuration of OH-2 in β-D-glucopyranoside and (2) distinguishing OH-4 and OH-6 from OH-3 in the β-D-mannopyranoside to introduce the bisecting GlcNAc residue.

AB - Convenient synthesis of an N-glycan octasaccharide (A) of the bisecting type was described. The stable and easily prepared orthoester F, 3 -O-chloroacetyl-4 ,6 -O-benzylidene-α-D-glucopyranose 1, 2 (chloromethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-3, 6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosylazide-4 -yl orthoacetate), was designed as the key intermediate with two advantages: (1) distinguishing OH-2 from OH-3 in β-D-glucopyranoside to construct the central β-D-mannopyranoside by inverting the configuration of OH-2 in β-D-glucopyranoside and (2) distinguishing OH-4 and OH-6 from OH-3 in the β-D-mannopyranoside to introduce the bisecting GlcNAc residue.

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DO - 10.1021/jo900016j

M3 - Article

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AN - SCOPUS:64149109669

SN - 0022-3263

VL - 74

SP - 2508

EP - 2515

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 6

ER -

Convenient synthesis of an N-glycan octasaccharide of the bisecting type

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