Reaction:JCGG-RAC0002403

JCGG ID		JCGG-RAC0002403
Submitter		The Noguchi Institute
Reaction ID		R-0000-002403
Regist Date		2012/06/21 19:10:11
REACTANT
MOLECULE ID		JCGG-COM0003124 (Reaction Tree)
	Reactant Type	thioglycoside
	Mol	100 micro mole
MOLECULE ID		JCGG-COM0003126 (Reaction Tree)
	Reactant Type	acceptor (in CH2Cl2)
	Mol	50 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-COM0003121
	Reactant Type	1-octene
	Mol	1 mmol
PRODUCT
MOLECULE ID		JCGG-COM0003128 (Reaction Tree)
	Yield	79%
REACTION DETAIL
Reaction Time		30 minutes, 5 + 5 minutes, 2.5 hours
Reaction Temp		-65 to -60 degree C, -78 degree C, -60 degree C
Solvent		distilled CH2Cl2, distilled CH2Cl2, distilled CH2Cl2
Comment		1) +all except 1-octene and acceptor, 2) +1-octene, 3) +acceptor
		Before the reaction, thioglycoside, BSP, and MS 4A were mixed and stirred for 0.5 hour at room temperature and then for 5 minutes at -65 degree in Celsius.
		MS 4A was included in the solvent.
		1-octene was added 5 minutes after the initiation of the reaction. (second phase)
		acceptor was added dropwise.
COMMENT
Keywords: xylomannan, antifreeze, Alaskan beetle, Upis ceramboides
There are multiple phases in this reaction.
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