JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002850
Submitter
The Noguchi Institute
Reaction ID
R-0000-002850
Regist Date
2012/06/21 19:58:10
REACTANT
MOLECULE ID
JCGG-COM0003736 (Reaction Tree)
Reactant Type
donor
Mol
0.21 mmol
MOLECULE ID
JCGG-COM0003737 (Reaction Tree)
Reactant Type
acceptor
Mol
0.23 mmol
MOLECULE ID
JCGG-COM0001843
Reactant Type
Cp2ZrCl2
Mol
0.41 mmol
MOLECULE ID
JCGG-COM0000032
Reactant Type
AgClO4
Mol
0.82 mmol
PRODUCT
MOLECULE ID
JCGG-COM0003738 (Reaction Tree)
Product Type
alpha
Yield
85%(alpha/beta=1/49)
MOLECULE ID
JCGG-COM0003739 (Reaction Tree)
Product Type
beta
Yield
85%(alpha/beta=1/49)
REACTION DETAIL
Reaction Time
30 minutes, 1 hour, 2.5 hours
Reaction Temp
room temp, -60 degree C, -50 degree C
Solvent
anhydrous CH2Cl2 (4.6mL), anhydrous CH2Cl2 (4.6+5mL), anhydrous CH2Cl2 (4.6+5mL)
Comment
1) Cp2ZrCl2+AgClO4, MS 4A, 2) +donor, acceptor, 3) temperature change
MS 4A was included in the solvent.
COMMENT
Keywords: Biantennary, N-glycans, LacNAc, LacdiNAc, SPPS
There are multiple phases in this reaction.
REFERENCE
Reference Id
REF-0000-000371
Issn
Electronic
Doi
10.1021/jo200149d
PubMed ID
21612260
Journal Name
The Journal of organic chemistry. (2011) 76 (13): 5229-39.
Article Title
Synthesis of biantennary complex-type nonasaccharyl asn building blocks for solid-phase glycopeptide synthesis.
Author
Masashi, Hagiwara; Mizuki, Dohi; Yuko, Nakahara; Keiko, Komatsu; Yuya, Asahina; Akiharu, Ueki; Hironobu, Hojo; Yoshiaki, Nakahara; Yukishige, Ito
Affiliation
Department of Applied Biochemistry, Institute of Glycoscience, Tokai University, 4-1-1 Kitakaname, Hiratsuka-shi, Kanagawa 259-1292, Japan.
Reference Id
REF-0000-000372
Source
J. Org. Chem. 2011, 76, 5229-5239
Doi
10.1021/jo200149d

©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST)