JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002416
Submitter
The Noguchi Institute
Reaction ID
R-0000-002416
Regist Date
2012/06/21 19:12:21
REACTANT
MOLECULE ID
JCGG-COM0003141 (Reaction Tree)
Reactant Type
thiomannopyranoside
Mol
0.3 mmol
MOLECULE ID
JCGG-COM0003118 (Reaction Tree)
Skeleton
JCGG-STR031571
Reactant Type
xylopyranoside
Mol
0.33 mmol
MOLECULE ID
JCGG-COM0002535
Reactant Type
BSP
Mol
0.36 mmol
MOLECULE ID
JCGG-COM0002536
Reactant Type
TTBP
Mol
0.45 mmol
MOLECULE ID
JCGG-COM0000761
Reactant Type
Tf2O
Mol
0.36 mmol
PRODUCT
MOLECULE ID
JCGG-COM0003143 (Reaction Tree)
Yield
84%
REACTION DETAIL
Reaction Time
30 minutes, 2.5 hours
Reaction Temp
-65 to -60 degree C, -60 degree C
Solvent
distilled CH2Cl2, distilled CH2Cl2
Comment
1) +all except xylopyranoside, 2) +xylopyranoside
Before the reaction, thiomannopyranoside, BSP, TTBP, and MS 4A were mixed and stirred for 30 minutes at room temperature and then for 5 minutes at -65 degree in Celsius.
MS 4A was included in the solvent.
Both Tf2O and xylopyranoside were added dropwise.
COMMENT
Keywords: xylomannan, antifreeze, Alaskan beetle, Upis ceramboides
There are multiple phases in this reaction.
ATTENTION: There are typos in the written method. (for compound 25 and 26, protocols and xylopyranosides are assigned inversely)
REFERENCE
Reference Id
REF-0000-000339
Issn
Electronic
Doi
10.1021/jo201780e
PubMed ID
21955117
Journal Name
The Journal of organic chemistry. (2011) 76 (21): 8611-20.
Article Title
Synthesis and structural verification of the xylomannan antifreeze substance from the freeze-tolerant Alaskan beetle Upis ceramboides.
Author
David, Crich; Md Yeajur, Rahaman
Affiliation
Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, United States. dcrich@chem.wayne.edu
Reference Id
REF-0000-000340
Source
J. Org. Chem. 2011, 76, 8611-8620
Doi
10.1021/jo201780e

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