JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002848
Submitter
The Noguchi Institute
Reaction ID
R-0000-002848
Regist Date
2012/06/21 19:57:43
REACTANT
MOLECULE ID
JCGG-COM0003732 (Reaction Tree)
Reactant Type
donor
Mol
1.79 mmol
MOLECULE ID
JCGG-COM0003733 (Reaction Tree)
Reactant Type
acceptor (in 10 mL of anhydrous CH2Cl2)
Mol
0.89 mmol
MOLECULE ID
JCGG-COM0002535
Reactant Type
BSP
Mol
2.67 mmol
MOLECULE ID
JCGG-COM0002536
Reactant Type
TTBP
Mol
3.58 mmol
MOLECULE ID
JCGG-COM0000761
Reactant Type
Tf2O
Mol
1.98 mmol
PRODUCT
MOLECULE ID
JCGG-COM0003734 (Reaction Tree)
Yield
73%
REACTION DETAIL
Reaction Time
30 minutes, 20 minutes, 2 days
Reaction Temp
-60 degree C, -60 degree C, -60 degree C
Solvent
anhydrous CH2Cl2 (35mL), anhydrous CH2Cl2 (35mL), anhydrous CH2Cl2 (35mL)
Comment
1) donor+BSP, TTBP, MS 4A, 2) +Tf2O, 3) +acceptor
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)