HuagongsheHuagongshe Chemistry Print Report · For research reference only
Bis(methoxymethyl)ether → L-Ascorbic Acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Bis(methoxymethyl)ether | HCID 12362 | — |
| Reactant | 5-(2,2-dimethyl-1,3-dioxolan-4-yl)-3,4-dihydroxy-2(5H)-furanone | HCID 54676508 | — |
| Product | L-Ascorbic Acid | HCID 54670067 | 32% |
Reaction Steps
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%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09295630B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-0209aeea27de45708004f0adc1b0d212 |
| Source note | uspto-grants-2016_03 |