Ethylene Oxide → (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Reaction equation

[CH2:1]1[O:3][CH2:2]1.C1[O:7]C1C.[C:8]1(=O)[O:15][C:13](=[O:14])[CH:11]([OH:12])[CH:9]1[OH:10]>>[O:14]=[CH:13][C@@H:11]([C@H:9]([C@@H:8]([C@@H:2]([CH2:1][OH:3])[OH:7])[OH:15])[OH:10])[OH:12]

Participants

Reactant 3

HCID 6354Ethylene Oxide

HCID 6378Propylene Oxide

HCID 11389406Dihydro-3,4-dihydroxy-2,5-furandione

Product 1

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalYield 20%

Procedure

1 mol of glucose was addition-polymerized with 25 mol of ethylene oxide and 25 mol of propylene oxide, the obtained glucose-polyoxyalkylene glycol ether compound was reacted with 5 mol of tartaric anhydride to form a half ester, and the ester was reacted with 5 mol of N-hydroxyglutal imide to prepare crosslinking agent 5. ##STR12##

Sources & evidence

ORD record: ord-16d8c2264ea24426a85bae6bdfdb3a49
Source dataset: uspto-grants-1989_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04839345

Reaction notes

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