(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → Demannose

HRID 426970

Reaction equation

HRID 426970 reaction equation
O=C[C@@H]([C@H]([C@@H](CO)O)O)O.[O:11]=[CH:12][C@@H:13]([C@H:15]([C@@H:17]([C@@H:19]([CH2:21][OH:22])[OH:20])[OH:18])[OH:16])[OH:14]>>[O:11]=[CH:12][C@H:13]([C@H:15]([C@@H:17]([C@@H:19]([CH2:21][OH:22])[OH:20])[OH:18])[OH:16])[OH:14]

Participants

3

Reactant 2

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 644160aldehydo-D-Xylose

Product 1

HCID 161658Demannose

Conditions

Temperature
80 °C

Procedure

A mixture of 5.7 g (38.4 mmole) of D-xylose of mp. 153° C. and 6.9 g (38.4 mmole) of D-glucose of mp. 143° C. is heated to approximately 80° C. with 52.7 g (176.8 mmole) of BEPDIB. The readily volatile constituents are then removed in vacuo (10-3Torr). Subsequent distillation gives 7.3 g of bp. 78° C./10-3Torr in addition to 11 g of yellowish residue.

Workup

  1. customThe readily volatile constituents are then removed in vacuo (10-3Torr)
  2. distillationSubsequent distillation
  3. customgives 7.3 g of bp. 78° C./10-3Torr

Sources & evidence

ORD record
ord-a57f12c0dd8146639e6a128631e27211
Source dataset
uspto-grants-1979_10
Patent number
US04172195

Linked notes

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