Reaction:JCGG-RAC0002729

JCGG ID		JCGG-RAC0002729
Submitter		The Noguchi Institute
Reaction ID		R-0000-002729
Regist Date		2012/06/21 19:43:38
REACTANT
MOLECULE ID		JCGG-COM0003567 (Reaction Tree)
	Reactant Type	(2R,3R,4R,5S,6S)-2-(allyloxy)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran (sugar)
	Mol	1.2 mmol
MOLECULE ID		JCGG-COM0003568
	Reactant Type	BH3*Me2S (2 M)
	Volume	0.3 mL
MOLECULE ID		JCGG-COM0000643
	Reactant Type	EtOH
	Volume	0.4 mL
MOLECULE ID		JCGG-COM0000418
	Reactant Type	NaOH (3 N)
	Volume	0.18 mL
MOLECULE ID		JCGG-COM0000421
	Reactant Type	H2O2 (35%)
	Volume	0.2 mL
PRODUCT
MOLECULE ID		JCGG-COM0003569 (Reaction Tree)
	Yield	88%
REACTION DETAIL
Reaction Time		1.5 hours, overnight, 1 hour
Reaction Temp		room temp, 0 to 5 degree C, 80 degree C
Solvent		NOT specified, EtOH (0.4mL), EtOH (0.4mL)
Comment		1) sugar+BH3*Me2S, 2) +EtOH, NaOH, H2O2, 3) temperature change
		The reactants were mixed at 0 degree in Celsius before stirred at room temperature. (first phase)
COMMENT
Keywords: trityl, photolabile, PPGs, electron-donating substituents, m-dimethylamino, photochemical deprotection
The reaction is explained in text only.
There are multiple phases in this reaction.
ATTENTION: There is a typo in the scheme. (3,4,5-tris(benzyloxy)-2-methyl-6-pent-4-enyloxytetrahydropyran should be (2R,3R,4R,5S,6S)-2-(allyloxy)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran)
For aglycon: O-allyl should be more plausible than O-4-pentenyl
REFERENCE
Reference Id		REF-0000-000365
	Issn	Electronic
	Doi	10.1021/jo200692c
	PubMed ID	21612261
	Journal Name	The Journal of organic chemistry. (2011) 76 (15): 5873-81.
	Article Title	Development of trityl-based photolabile hydroxyl protecting groups.
	Author	Lei, Zhou; Haishen, Yang; Pengfei, Wang
	Affiliation	Department of Chemistry, University of Alabama at Birmingham, 901 14th Street South, Birmingham, Alabama 35294, USA.
Reference Id		REF-0000-000366
	Source	J. Org. Chem. 2011, 76, 5873-5881
	Doi	10.1021/jo200692c