Acetic Acid → (2S,3R,4S)-2-methyl-3,4-dihydro-2H-pyran-3,4-diol

HRID 1154884ノート

反応式

HRID 1154884 の反応式
[CH3:1][C@@H:2]1[O:7][CH:6]=[CH:5][C@H:4]([O:8]C(C)=O)[C@H:3]1[O:12]C(C)=O.C[O-].[Na+].C(O)(=O)C>CO>[CH3:1][C@@H:2]1[O:7][CH:6]=[CH:5][C@H:4]([OH:8])[C@H:3]1[OH:12]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 2734733L-arabino-Hex-1-enitol, 1,5-anhydro-2,6-dideoxy-, diacetateHCID 10942334Sodium Methoxide

生成物 1

HCID 10986248(2S,3R,4S)-2-methyl-3,4-dihydro-2H-pyran-3,4-diol

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

10 grams of 3,4-di-O-acetyl-L-rhamnal is dissolved in 100 milliliters of methanol, and the pH is adjusted to 8 to 9 by the dropwise addition of a freshly prepared solution of sodium methoxide in methanol. The flask is sealed and allowed to stand at 0°-5° C. overnight after which time deacetylation is complete. The solution is neutralized by the careful dropwise addition of glacial acetic acid, and then the solvent is removed under reduced pressure. The resulting clear syrup is co-evaporated several times with toluene to remove any excess acetic acid, and the syrup crystallizes during these evaporations to give L-rhamnal. The yield of this compound is 6 grams.

後処理

  1. customThe flask is sealed
  2. customthe solvent is removed under reduced pressure
  3. customto remove any excess acetic acid
  4. customthe syrup crystallizes during these evaporations

出典と根拠

ORDレコード
ord-66bde99a6948477a94500858fced76a5
出典データセット
uspto-grants-1981_11
特許番号
US04298726

反応ノート

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