N-Methyl-D-glucamine → 6-[(3-{3-[Dimethyl-(2-trimethylsilanyl-ethyl)-silanyl]-propoxy}-2-hydroxy-propyl)-methyl-amino]-hexane-1,2,3,4,5-pentaol

HRID 1361114Notes

Reaction equation

[CH3:1][NH:2][CH2:3][C@@H:4]([C@H:6]([C@@H:8]([C@@H:10]([CH2:12][OH:13])[OH:11])[OH:9])[OH:7])[OH:5].[CH3:14][Si:15]([CH3:30])([CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH:21]1[CH2:23][O:22]1>C(O)C>[CH3:14][Si:15]([CH3:30])([CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH:21]([OH:22])[CH2:23][N:2]([CH3:1])[CH2:3][CH:4]([OH:5])[CH:6]([OH:7])[CH:8]([OH:9])[CH:10]([OH:11])[CH2:12][OH:13]

Participants

Conditions

Temperature: 70 °C

Procedure

N-methyl-D-glucamine (1.42 g; 7.28 mMol) and 40 mL of ethanol were charged to a 100 mL RB flask equipped with a magnetic stirrer. The mixture was stirred and heated to 70° C. 2-{3-[Dimethyl-(2-trimethylsilanyl-ethyl)-silanyl]-propoxymethyl}-oxirane 8 (2 g; 7.28 mMol) mixed with 10 g ethanol was placed in an addition funnel and added dropwise to the flask. The mixture was stirred and maintained at 70° C. for an additional 4 hours. Ethanol was stripped off on the rotovap. The mixture was distilled under vacuum to remove impurities.

Workup

customequipped with a magnetic stirrer
customwas placed in an addition funnel
additionadded dropwise to the flask
stirringThe mixture was stirred
temperaturemaintained at 70° C. for an additional 4 hours
distillationThe mixture was distilled under vacuum
customto remove impurities

Sources & evidence

ORD record: ord-d609e32969874cd98e96c24a3a4a0f03
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879916B2

Reaction notes

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