Reaction:JCGG-RAC0002413

JCGG ID		JCGG-RAC0002413
Submitter		The Noguchi Institute
Reaction ID		R-0000-002413
Regist Date		2012/06/21 19:12:01
REACTANT
MOLECULE ID		JCGG-COM0003124 (Reaction Tree)
	Reactant Type	thioglycoside
	Mol	100 micro mole
MOLECULE ID		JCGG-COM0003138 (Reaction Tree)
	Reactant Type	acceptor (in CH2Cl2)
	Mol	100 micro mole
MOLECULE ID		JCGG-COM0002535
	Reactant Type	BSP
	Mol	120 micro mole
MOLECULE ID		JCGG-COM0000761
	Reactant Type	Tf2O
	Mol	120 micro mole
MOLECULE ID		JCGG-COM0000530
	Reactant Type	NaOMe
	Mol	NOT specified
PRODUCT
MOLECULE ID		JCGG-COM0003139 (Reaction Tree)
	Yield	72%
REACTION DETAIL
Reaction Time		30 minutes, 2.5 hours, NOT specified
Reaction Temp		-65 to -60 degree C, -60 degree C, NOT specified
Solvent		CH2Cl2, CH2Cl2, MeOH
Comment		1) +all except acceptor and NaOMe, 2) +acceptor, 3) +NaOMe
		Before the reaction, thioglycoside, BSP, 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.
		The reactants were mixed at -70 degree in Celsius before stirred at -60 degree. (second phase)
		Both Tf2O and acceptor were added dropwise.
COMMENT
Keywords: xylomannan, antifreeze, Alaskan beetle, Upis ceramboides
There are multiple phases in this reaction.
ATTENTION: There is a typo in the scheme. (compound 8 should be 7)
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