Calcium Gluconate → Tri-O-acetyl-D-glucal

HRID 2093249

반응식

HRID 2093249 반응식
[CH2:1]([C@@H:4]([OH:11])[C@H:5]([OH:10])[C@H:6](O)[CH2:7][OH:8])[CH:2]=[O:3].[O:12]=[CH:13][C@@H:14]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[O:24]=[CH:25][C@H:26]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[O:36]=[C:37]([O-])[C@@H:38]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[Ca+2].O=C([O-])[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.O=C[C@H]([C@@H]([C@@H](CO)O)O)O.Cl.OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1N.C(N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1O)(=O)C.BrBr>>[C:13]([O:10][C@H:5]1[C@H:4]([O:11][C:25](=[O:24])[CH3:26])[C@@H:1]([CH2:2][O:3][C:37](=[O:36])[CH3:38])[O:8][CH:7]=[CH:6]1)(=[O:12])[CH3:14]

참가 물질

9

반응물 8

HCID 9290Calcium GluconateHCID 24408BromineHCID 66308D-ArabinoseHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal3회HCID 1082232-DeoxyglucoseHCID 161658Demannose2회HCID 439174N-Acetyl-D-GlucosamineHCID 2723635(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochloride

생성물 1

HCID 688303Tri-O-acetyl-D-glucal

실험 절차

Production of 2DG can be carried out using any known method. For example, 2-DG can be prepared from various starting materials such as D-glucose, D-mannose, calcium D-gluconate, D-arabinose, D-glucosamine hydrochloride, N-acetyl glucosamine, chitin, and chitosan and carboxymethylchitosan. Preparation methods vary with various starting materials. For example, D-glucose can be methylated and brominated, followed by debromination and acid hydrolysis to yield β-2DG. Bergmann et. al. (1992) Berichte der Deutschen Chemischen Gesellschaft Jahrg. 55:158-72. D-glucose or D-mannose can be treated with bromine and acetyl, followed by a Fischer procedure (Fischer et al. (1914) (Berichte der Deutschen Chemischen Gesellschaft Jahrg. 47:196-210), to yield 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol, which is reacted with bromine, then reduced to remove the acetyl group, yielding 2DG (Arita et al. (1972) Bull. Chem. Soc. Japan 45:567-69). The 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol intermediate can be treated with N-bromosuccinimide, followed by hydrogenation and deacetylation to yield 2DG. Monneret and Choay (1981) Carbohydr. Res. 96:299-305. D-glucose can be reacted with ethanethiol and benzoyl chloride, followed by dehydrogenation, reduction, and deprotection to give 2-DG. Wong and Gray (1980) Carbohydr. Res. 80:87-98). Glucal can be deacetylated by reacting with sulfuric acid to give 2-DG with an overall yield of 35%. Overend et al. (1949) J. Chem. Soc., 1:2841-45. D-arabinose can be treated with nitromethane and an acetylating agent, followed by treatment with diluted sodium hydroxide, to yield a-2-DG. Sowden and Fischer (1947)J. Am. Chem. Soc. 69:1048-50. D-arabinose can be condensed, reduced with acetone, then reacted with trifluoromethanesulfonic anhydride, to yield a product that is then reacted with sodium cyanide, followed by hydrogenation, reduction, and hydrolysis, yielding 2-DG. Shiue et al. (1979) Carbohydr. Res. 74:323-26.

후처리

  1. customPreparation methods
  2. customfollowed by debromination and acid hydrolysis
  3. customto yield β-2DG

출처 및 근거

ORD 기록
ord-2bd64e11beab44089c2f3d3b7aeed252
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445021B2

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