JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002148
Submitter
The Noguchi Institute
Reaction ID
R-0000-002148
Regist Date
2012/06/21 18:40:58
REACTANT
MOLECULE ID
JCGG-COM0002793 (Reaction Tree)
Reactant Type
intermediate
Mol
0.02 mmol
MOLECULE ID
JCGG-COM0000746
Reactant Type
1H-tetrazole (0.45 M in MeCN)
Mol
0.1 mmol
MOLECULE ID
JCGG-COM0000747
Reactant Type
(BnO)2PN(i-Pr)2
Mol
0.08 mmol
MOLECULE ID
JCGG-COM0002531
Reactant Type
MCPBA
Mol
0.08 mmol
PRODUCT
MOLECULE ID
JCGG-COM0002794 (Reaction Tree)
Yield
95%
REACTION DETAIL
Reaction Time
2 hours, 3 hours, 1 hour
Reaction Temp
room temp, room temp, room temp
Solvent
CH2Cl2, CH2Cl2, CH2Cl2
Comment
1) 27+1H-tetrazole, MS 4A, 2) +(BnO)2PN(i-Pr)2, 3) +MCPBA
MS 4A was included in the solvent.
COMMENT
Keywords: mannose-6-phosphate, M6P, N-linked glycans, eukaryotic cells, N-acetylglucosamine, GlcNAc, sequential deprotection
There are multiple phases in this reaction.
REFERENCE
Reference Id
REF-0000-000321
Issn
Electronic
Doi
10.1021/jo2010999
PubMed ID
21955083
Journal Name
The Journal of organic chemistry. (2011) 76 (21): 8682-9.
Article Title
Chemical synthesis of N-linked glycans carrying both mannose-6-phosphate and GlcNAc-mannose-6-phosphate motifs.
Author
Yunpeng, Liu; Gong, Chen
Affiliation
Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, United States.
Reference Id
REF-0000-000322
Source
J. Org. Chem., 2011, 76 (21), pp 8682-8689
Doi
10.1021/jo2010999

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