Bis(methoxymethyl)ether → L-Ascorbic Acid

HRID 929324Notes

Reaction equation

HRID 929324 reaction equation
CC1(C)[O:6][CH:5]([CH:7]2[O:12][C:10](=[O:11])[C:9]([OH:13])=[C:8]2[OH:14])[CH2:4][O:3]1.COCOCOC>>[O:11]=[C:10]1[O:12][C@H:7]([C@H:5]([CH2:4][OH:3])[OH:6])[C:8]([OH:14])=[C:9]1[OH:13]

Participants

3

Reactant 2

HCID 12362Bis(methoxymethyl)etherHCID 546765085-(2,2-dimethyl-1,3-dioxolan-4-yl)-3,4-dihydroxy-2(5H)-furanone

Product 1

HCID 54670067L-Ascorbic AcidYield 32%

Procedure

5,6-O-Isopropylidene-L-ascorbic acid was protected in the form of methoxymethyl ether according to the procedure of Kulkami et al. (M. G. Kulkami and S. R. Thopate, Tetrahedron, 1996, 52, 1293). A Mitsunobu reaction (C. Cena et al. Bioorg. Med. Chem. 2008, 16, 5199) with 1,1′,2-trisnorsqualenol followed by hydrolysis gives 2-squalenyl ascorbic acid (2-SQ Vit C) at an overall yield of 32%.

Workup

  1. customA Mitsunobu reaction (C. Cena et al. Bioorg. Med. Chem. 2008, 16, 5199)
  2. customwith 1,1′,2-trisnorsqualenol followed by hydrolysis

Sources & evidence

ORD record
ord-0209aeea27de45708004f0adc1b0d212
Source dataset
uspto-grants-2016_03
Patent number
US09295630B2

Reaction notes

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