US 12,391,719 B2
Methods for producing stereoisomerically enriched carbohydrate-based surfactants
Jeanne E. Pemberton, Tucson, AZ (US); and Tyler Roberts, Tucson, AZ (US)
Assigned to ARIZONA BOARD OF REGENTS ON BEHALF OF THE UNIVERSITY OF ARIZONA, Tucson, AZ (US)
Filed by ARIZONA BOARD OF REGENTS ON BEHALF OF THE UNIVERSITY OF ARIZONA, Tucson, AZ (US)
Filed on Sep. 29, 2021, as Appl. No. 17/489,477.
Application 17/489,477 is a continuation in part of application No. 17/473,999, filed on Sep. 13, 2021, abandoned.
Application 17/473,999 is a continuation of application No. 15/358,159, filed on Nov. 22, 2016, granted, now 11,117,914.
Application 15/358,159 is a continuation in part of application No. 14/041,251, filed on Sep. 30, 2013, granted, now 9,499,575, issued on Nov. 22, 2016.
Claims priority of provisional application 61/796,653, filed on Nov. 16, 2012.
Prior Publication US 2022/0017556 A1, Jan. 20, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07H 15/04 (2006.01); C07F 3/00 (2006.01); C07F 9/94 (2006.01); C07H 1/00 (2006.01); C07H 15/06 (2006.01); C07H 15/14 (2006.01)
CPC C07H 15/14 (2013.01) [C07F 3/003 (2013.01); C07F 9/94 (2013.01); C07H 1/00 (2013.01); C07H 15/04 (2013.01); C07H 15/06 (2013.01)] 9 Claims
 
1. A stereoselective method for producing a protected carbohydrate-based surfactant of the formula:

OG Complex Work Unit Chemistry
said method comprising: contacting an enantiomerically enriched alcohol compound of the formula:

OG Complex Work Unit Chemistry
with a protected carbohydrate under conditions sufficient to form a covalent bond between said carbohydrate and said compound of Formula A to produce said protected carbohydrate-based surfactant of Formula I, wherein
a carbohydrate of said protected carbohydrate is selected from the group consisting of a monosaccharide, a disaccharide, and a trisaccharide;
Y1 is selected from the group consisting of hydrogen, ethylenyl, ethynyl, halide, —SH, —NH2, and —CO2Rs;
Rz1 is hydrogen, alkyl, benzyl, or a carboxylic acid protecting group;
Rs is hydrogen or alkyl;
x1 is an integer from 5 to 30; and
is a chiral center.