Sodium Bicarbonate → HCID 12818663, compound

HRID 904107Notes

Reaction equation

HRID 904107 reaction equation
[C:1]([O:9][CH2:10][C@@H:11]([OH:22])[C@H:12]1[O:17]C(O)[C@H:14]([OH:18])[C@H:13]1[N:19]=[N+:20]=[N-:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I([O-])(=O)(=O)=O.[Na+].C([O-])(O)=O.[Na+]>>[C:1]([O:9][CH2:10][C@H:11]1[O:22][CH:14]([OH:18])[C@@H:13]([N:19]=[N+:20]=[N-:21])[C@@H:12]1[OH:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 12818661HCID 12818661, compoundHCID 23667635Sodium periodate

Product 1

HCID 12818663HCID 12818663, compound

Procedure

Benzoylation of 1,2-O-isopropylidene-3-azido-3-deoxy-α-D-glucofuranose with 1.05 molar equivalent of benzoyl chloride gives a greater than 90% yield of 1,2-O-isopropylidene-6-O-benzoyl-3-azido-3-deoxy-α-D-glucofuranose (1). A sample of 1 is purified on silica gel (CHCl3 -ether; 3:1), NMR (CDCl3, TMS internal standard) δ 7.36-8.18 (2m, 5, aromatic), 5.93 (d, 1, J1,2 =3.5 Hz, H-1), 4.67 (d, 1, J1,2 =3.5 Hz, H-2), 4.25-4.80 (m, 5, H-3,4,5,6), 1.50, 1.33 (2s, 6, 2CH3). Crude 1, which contains a small amount of 5,6-di-O-benzoate and a trace of 5-O-benzoate derivatives, is hydrolyzed in dioxane-water (1:1) with Dowex 50 [H+ ] ion exchange resin to give 6-O-benzoyl-3-azido-3-deoxy-D-glucofuranose (2). Compound 2, which gives a poorly resolved NMR spectrum, is oxidized with sodium metaperiodate at 22-28 degrees C. for 3 hr., followed by treatment with NaHCO3 (to hydrolyze the formyl group) overnight to give 5-O-benzoyl-2-azido-2-deoxy-D-arabinofuranose (3), which is purified by silica gel chromatography (CH2Cl2 -ether; 3:1).

Workup

  1. customA sample of 1 is purified on silica gel (CHCl3 -ether; 3:1), NMR (CDCl3, TMS internal standard) δ 7.36-8.18 (2m, 5, aromatic), 5.93 (d, 1, J1,2 =3.5 Hz, H-1), 4.67 (d, 1, J1,2 =3.5 Hz, H-2), 4.25-4.80 (m, 5, H-3,4,5,6), 1.50, 1.33 (2s, 6, 2CH3)
  2. customto give 6-O-benzoyl-3-azido-3-deoxy-D-glucofuranose (2)
  3. customovernight

Sources & evidence

ORD record
ord-6178fd0294b74ae4a1ce35e090b8fe10
Source dataset
uspto-grants-1980_10
Patent number
US04230698

Reaction notes

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