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

HRID 426972Notes

Reaction equation

HRID 426972 reaction equation
[CH2:1]([OH:12])[C@H:2]([C@H:4]([C@@H:6]([C@@H:8]([CH2:10][OH:11])[OH:9])[OH:7])[OH:5])[OH:3].C(O)[C@@H]([C@H]([C@@H](CO)O)O)O>>[O:11]=[CH:10][C@@H:8]([C@H:6]([C@@H:4]([C@@H:2]([CH2:1][OH:12])[OH:3])[OH:5])[OH:7])[OH:9]

Participants

3

Reactant 2

HCID 6251MannitolHCID 178418489HCID 178418489, compound

Product 1

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Procedure

A mixture of 7.46 g (41 mmole) of D-mannitol and 6.2 g (41 mmole) of xylitol is heated for 30 minutes to 80° C. with 67.5 g (227 mmole) of BEPDIB. After the readily volatile constituents have been distilled off in vacuo (10-3Torr), 11.6 g (96%) of bp. 108° C./10-3Torr and [α]D20 9.7 (c=6, CCl4) and 9.2 g (91%) of viscous residue are obtained.

Workup

  1. temperatureis heated for 30 minutes to 80° C. with 67.5 g (227 mmole) of BEPDIB
  2. distillationAfter the readily volatile constituents have been distilled off in vacuo (10-3Torr), 11.6 g (96%) of bp. 108° C./10-3Torr and [α]D20 9.7 (c=6, CCl4) and 9.2 g (91%) of viscous residue
  3. customare obtained

Sources & evidence

ORD record
ord-11312da6a2834eb4a44313c189813ae9
Source dataset
uspto-grants-1979_10
Patent number
US04172195

Reaction notes

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