JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002851
Submitter
The Noguchi Institute
Reaction ID
R-0000-002851
Regist Date
2012/06/21 19:58:19
REACTANT
MOLECULE ID
JCGG-COM0003740 (Reaction Tree)
Reactant Type
donor
Mol
85 micro mole
MOLECULE ID
JCGG-COM0003737 (Reaction Tree)
Reactant Type
acceptor
Mol
89 micro mole
MOLECULE ID
JCGG-COM0000009
Reactant Type
TMSOTf (2% in CH2Cl2)
Mol
4.3 micro mole
PRODUCT
MOLECULE ID
JCGG-COM0003738 (Reaction Tree)
Product Type
alpha
Yield
79%(alpha/beta=1/99)
MOLECULE ID
JCGG-COM0003739 (Reaction Tree)
Product Type
beta
Yield
79%(alpha/beta=1/99)
REACTION DETAIL
Reaction Time
1.5 hours, 0.5 hour
Reaction Temp
-78 degree C, -40 degree C
Solvent
anhydrous CH2Cl2 (3mL), anhydrous CH2Cl2 (3mL)
Comment
1) +all, 2) temperature change
MS AW300 was included in the solvent.
The addition of TMSOTf was performed after the addition of all the other reactants.
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

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