Acetic Acid → HCID 15885012, compound

HRID 1421355Notes

Reaction equation

HRID 1421355 reaction equation
[Si]([O:8][C@@H:9]1[C@@H:16]([NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[C@H:15]([CH3:24])[O:14][C@@H:11](OC)[C@@H:10]1[F:25])(C(C)(C)C)(C)C.[C:26](OC(=O)C)(=[O:28])[CH3:27].S(=O)(=O)(O)O.[C:38]([OH:41])(=[O:40])[CH3:39]>>[C:38]([O:41][CH:11]1[O:14][C@@H:15]([CH3:24])[C@H:16]([NH:17][C:18](=[O:23])[C:19]([F:20])([F:21])[F:22])[C@@H:9]([O:8][C:26](=[O:28])[CH3:27])[C@H:10]1[F:25])(=[O:40])[CH3:39]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 15885011HCID 15885011, compound

Product 1

HCID 15885012HCID 15885012, compound

Procedure

Compound (7) is treated with a mixture of acetic anhydride, acetic acid and sulfuric acid at room temperature, thereby to effect simultaneously the removal of the 3-O-tert-butyldimethylsilyl group, demethylation and di-O-acetylation reactions, affording 1,3-di-O-acetyl-2,4,6-trideoxy-2-fluoro-4-(trifluoroacetylamino)-L-mannopyranose [Compound (8)] having the following formula ##STR15## The Compound (8) is a mixture or α-anomer [Compound (8-a)] and β-anomer [Compound (8-b)]. When Compound (8) is subjected to a silica gel column chromatography as developed with dichloromethane, the α-anomer [Compound (8-a)] and the β-anomer [Compound (8-b)] can be isolated from each other.

Workup

  1. customthe removal of the 3-O-tert-butyldimethylsilyl group, demethylation and di-O-acetylation reactions

Sources & evidence

ORD record
ord-6a44252f012241d4a644fa5f3ee35800
Source dataset
uspto-grants-2000_06
Patent number
US06075135

Reaction notes

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