The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.10034-20-5, Name is (2S,3R,4R,5S,6R)-6-(Acetoxymethyl)-3-aminotetrahydro-2H-pyran-2,4,5-triyl triacetate hydrochloride, molecular formula is C14H22ClNO9. In a Article,once mentioned of 10034-20-5, Safety of (2S,3R,4R,5S,6R)-6-(Acetoxymethyl)-3-aminotetrahydro-2H-pyran-2,4,5-triyl triacetate hydrochloride
The application of the 2-(chloroacetoxymethyl)benzoyl (CAMB) group to the O-protection of position 2 in glycosyl donors is described.Saponification of the phthalide and subsequent chloroacetylation of 2-(hydroxymethyl)benzoic acid (1) gave 2-(chloroacetoxymethyl)benzoic acid (2).Treatment of 2 with thionyl chloride afforded the acyl chloride 3.Acylation of O-2 of 1,3,4,6-tetra-O-acetyl-alpha-D-glucopyranose (4a), galactopyranose (4b) and of the amino group of 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-beta-D-glucopyranose (4c) afforded the fully protected pyranose derivatives 5a-c in high yields.Compounds 5a and 5b were converted with HBr in acetic acid into the corresponding 2-O-CAMB-protected bromides 6a, b in excellent yields.Silver trifluoromethanesulfonate promoted glycosylation of the latter with 2-hydroxyethyl benzoate yielded the beta-glycosides 8a (74percent) and 8b (69percent).Direct activation of the glucosamine derivative 5c with ferric chloride gave the glucoside 8c (54percent).Furthemore, the galactosyl bromide 6b was coupled with methyl 2,3,4-tri-O-benzoyl-beta-D-glucopyranoside (11) affording the 2′-O-CAMB-protected methyl glycoside disaccharide 12 (63percent).Similarly, condensation of the glucosyl bromide 6a with 4a gave the beta-(1–>2)-linked disaccharide 13 (45percent).Treatment of compounds 8a and 13 with thiourea resulted in the deblocked glycosides 9a and 14.Similar deprotection of 8b gave 2-benzoyloxyethyl 3,4,6-tri-O-acetyl-beta-D-galactopyranoside (9b) and the 2-O-<2(hydroxymethyl)benzoyl> derivative 10.Reaction of 8c with thiourea afforded solely the dechloroacetylated glucoside 9c. – Key Words: Glycosylation / Protecting groups / Benzoyl, 2-chloroacetoxymethyl-
Note that a catalyst decreases the activation energy for both the forward and the reverse reactions and hence accelerates both the forward and the reverse reactions.Safety of (2S,3R,4R,5S,6R)-6-(Acetoxymethyl)-3-aminotetrahydro-2H-pyran-2,4,5-triyl triacetate hydrochloride, you can also check out more blogs about10034-20-5
Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics