New synthesis of fucose
AssigneeGlycom A/S
InventorsNikolay Khanzhin, Julien Boutet, Filippo Bonaccorsi, Gyula Dekany
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Abstract
A process for converting D-glucose into L-fucose, where a first aspect of the disclosure relates to a method of making a compound of formula (1) wherein R is independently H, alkyl or phenyl or, preferably, wherein the two germinal R groups together with the carbon atom to which they are attached form a C3-s cycloalkylidene group, including the step of treating a compound of formula (2) wherein R is defined above and R1 is a sulphonate leaving group, with a reducing complex metal hydride and, preferably, a base to form the compound of formula (1); a compound of formula (13).
Claims32
A method of making a compound of formula 1
- wherein R is independently H, alkyl or phenyl or wherein the two germinal R groups together with the carbon atom to which they are attached form a C3-8 cycloalkylidene group,
- comprising the step of:
- treating a compound of formula 2
- wherein R is as defined above and R1 is a sulphonate leaving group,
- with a reducing complex metal hydride to form the compound of formula 1.
(canceled)
A compound of formula 13
- wherein the moiety
- is a highly lipophilic protecting group and wherein either:
- Ra and Re together form an oxygen bridge when Rb is OH or a sulphonate leaving group;
- or Ra is H and Re is OH when Rb is a sulphonate group,
- or formula 14
- wherein the moiety
- is a highly lipophilic protecting group, and wherein either:
- Rd is OH and Re is or Rd and Re together form an oxygen bridge.
(canceled)
Dependencies are inferred from the claim text.