D-Glucuronic Acid → 6-Aminohexane-1,2,3,4,5-pentol

HRID 1926572Notes

Reaction equation

HRID 1926572 reaction equation
OC1[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:3]1[NH:12]C(C)=O.[OH:16][CH:17]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O.C(OC)#N>>[CH2:3]([NH2:12])[CH:4]([OH:5])[CH:6]([OH:7])[CH:8]([OH:9])[CH:10]([OH:11])[CH2:17][OH:16]

Participants

4

Reactant 3

HCID 94715D-Glucuronic Acid2×HCID 137201Cyanic acid, methyl esterHCID 439174N-Acetyl-D-Glucosamine3×

Product 1

HCID 102666-Aminohexane-1,2,3,4,5-pentol

Procedure

1H NMR of IV, Na-salt (500 MHz, D2O, 2 mM NaHCO3, 30° C.): δ=5.473 (m, 2 —CH═CH— of DOPE), 5.328 (m, OCH2CHCH2O of DOPE), 4.574 and 4.473 (m, HA: H-1 of GlcNAc, H-1 of GlcA; CO—OCHCHCH2 of DOPE), 4.246 (dd, J=12.3 Hz, J=6.8 Hz, CO—OCHCHCH2 of DOPE), 4.027 (t, J=5.7 Hz, POCH2CH2N of DOPE), 3.95-3.34 (HA: H-2+H-6 of GlcNAc, H-2+H-5 of GlcA; POCH2CHCH2 of DOPE), 2.413 (m, 2 CH2COO of DOPE), 2.302 (m, 2 CH2CON), 2.049 (m, 2 CH2CH═CHCH2 of DOPE), 2.039 (m, NCOCH3 of GlcNAc), 1.630 (m, 2 CH2CH2CON and 2 CH2CH2COO of DOPE), 1.306 (m, —CH2— of DOPE), 0.892 (˜t, 2 CH3 of DOPE) ppm.

Sources & evidence

ORD record
ord-f85e0bec20ba422e85996eeded06ba90
Source dataset
uspto-grants-2012_05
Patent number
US08183214B2

Reaction notes

Loading…