JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0002422
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-002422
Regist Date
 2012/06/21 19:12:57
REACTANT
MOLECULE ID
 JCGG-COM0003149 (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-COM0003150 (Reaction Tree)
Yield
 82%
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: TTBP is mentioned in the written method, but it is not found in the scheme.
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)