Ethyl Acetate → (2'S,3'R,4'S,5'R,6'R)-3',4',5'-tris(benzyloxy)-6'-(benzyloxymethyl)-7-chloro-6-(4-ethylbenzyl)-2,2-dimethyl-3',4',5',6'-tetrahydrospiro[chroman-4,2'-pyran]

Participants

Role	Name	HCID	Charge
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	5-chloro-4-(4-ethylbenzyl)-2-((2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(2-methylallyl)tetrahydro-2H-pyran-2-yl)phenol	HCID 68792676	—
Catalyst	Silver(I) trifluoromethanesulfonate	HCID 76223	—
Solvent	1,1-Dichloroethane	HCID 6365	—
Product	(2'S,3'R,4'S,5'R,6'R)-3',4',5'-tris(benzyloxy)-6'-(benzyloxymethyl)-7-chloro-6-(4-ethylbenzyl)-2,2-dimethyl-3',4',5',6'-tetrahydrospiro[chroman-4,2'-pyran]	HCID 68794569	40%

Reaction Conditions

Temperature	70 °C

Reaction Steps

A mixture of 25 (48 mg, 58 μmol) and silver triflate (15 mg, 58 μmol) in dichloroethane (1 mL) was heated to 70° C. for 2 h. LC/MS indicated that the conversion was complete to give a new and less polar component. After cooling, the mixture was loaded onto a TLC plate and developed using 10% EtOAc in petroleum ether to give 56 (19 mg, 40%). LC/MS m/z 846 (M+Na), 824 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07795228B2
Source dataset	uspto-grants-2010_09
ORD ID	ord-1708eec37d344a43afc3012e6311fc19
Source note	uspto-grants-2010_09