HCID 10857507, compound → 3-Deoxy-L-manno-2-octulosonic acid

HRID 276095Notes

Reaction equation

HRID 276095 reaction equation
[CH2:1]1[C:6]([OH:10])([C:7]([OH:9])=[O:8])[O:5][C@H:4]([C@H:11]([OH:14])[CH2:12][OH:13])[C@H:3]([OH:15])[C@@H:2]1[OH:16]>O>[C:7]([OH:9])(=[O:8])[C:6]([CH2:1][C@@H:2]([C@@H:3]([C@H:4]([C@H:11]([CH2:12][OH:13])[OH:14])[OH:5])[OH:15])[OH:16])=[O:10]

Participants

3

Reactant 1

HCID 10857507HCID 10857507, compound2×

Product 1

HCID 454806473-Deoxy-L-manno-2-octulosonic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

The specific rotation and spectral data were obtained after L-KDO had been converted to its ammonium salt: [α]25D−37.2° (c 0.68, H2O) [for D-KDO:[α]27D+42.3° (c 1.7, H2O) Unger, Adv. Charbohydr. Chem. Biochem., 381:323 (1981); authentic sample from Sigma [α]25D+40.1° (c 2.1, H2O)]. Since KDO has an axial 5-OH group, it is known that it exists as a mixture of pyranose and furanose forms, and readily cyclizes to the corresponding lactone. The 1H and 13C NMR data of the predominant form are: 1H MMR (D2O) δ4.03 (1H, ddd, J4-3ax=13.0 Hz, J4-3eq=5.5 Hz, J4-5=3.0 Hz, H-4), 4.00 (1H, m, H-5) 3.87 (1H, dt, J7-8b=3.0 Hz, J7-6J7-8a=5.5 Hz, H-7), 3.84 (1H, m, H-6), 3.78 (1H, dd, J8b-8a=12.0 Hz, J8b-7=3.0 Hz, H-8b), 3.60 (1H, dd, J8a-8b=12.0 Hz, J8a-7=5.5 Hz, H-8a), 2.00 (1H, t, J3ax-3eq=J3ax-4=13.0 Hz, H-3ax), 1.86 (1H, dd, J3eq-3ax=13.0 Hz, J3eq-4=5.5 Hz, H-3eq). 13C NMR (D2O+CD3CN) δ177.3, 96.8, 72.0, 71.3, 67.0, 66.6, 63.4, 34.0. 1H and 13C NMR spectra were identical with those of D-KDO from Sigma. HRMS (FAB) calcd for C8H14O8Na(M+Na+) 261.0586, found 261.0591.

Workup

  1. customThe specific rotation and spectral data were obtained after L-KDO

Sources & evidence

ORD record
ord-565728a5e15b4cd0a2c5b3742b9ea599
Source dataset
uspto-grants-2002_03
Patent number
US06353095B1

Reaction notes

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