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D-Altritol → 1,5-dideoxy-1,1,1,5-tetrafluoro-L-altritol

HRID 862384
Notes
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Reaction equation

HRID 862384 reaction equation
C(O)[C@H]([C@@H]([C@@H]([C@@H](CO)O)O)O)O.C([O:20][C@@H:21]([C@H:28]([C@@H:37]([F:40])[CH2:38][OH:39])[O:29]CC1C=CC=CC=1)[C@@H:22]([OH:27])[C:23]([F:26])([F:25])[F:24])C1C=CC=CC=1.[H][H]>[Pd]>[F:24][C:23]([F:25])([F:26])[C@@H:22]([C@H:21]([C@H:28]([C@@H:37]([F:40])[CH2:38][OH:39])[OH:29])[OH:20])[OH:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 151263D-AltritolHCID 545685113,4-di-O-benzyl-1,5-dideoxy1,1,1,5-tetrafluoro-L-altritolHCID 178418361HCID 178418361, compound

Product 1

HCID 540937631,5-dideoxy-1,1,1,5-tetrafluoro-L-altritol

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Further, the aforesaid altritol Compound (10) is a new compound. When Compound (10) is reduced with hydrogen in the presence of a palladium catalyst under mild reaction conditions, the benzyl groups can be removed from Compound (10) to produce 1,5-dideoxy-1,1,1,5-tetrafluoro-L-altritol.

Workup

  1. customthe benzyl groups can be removed from Compound (10)

Sources & evidence

ORD record
ord-3120e467f6e54953a326918852ed62b8
Source dataset
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05719130

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes