5329-49-7

Upstream product

• 96796-56-4 1,2:3,4-di-O-isopropylidene-6,7-didehydro-α-D-galacto-oct-6(Z)-eno-1,5-pyranose 
• 115520-85-9 1-((2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propane-1,2,3-triol 
• 115520-84-8 methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-6(E)-eno-α-D-gluco-oct-1,5-pyranoside 
• 115520-85-9 methyl 2,3,4-tri-O-benzyl-L-threo-β-D-gluco-oct-1,5-pyranoside 
• 83051-88-1 methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 5399-48-4 (2S,3R,4S,5S,6R)-2-Methoxy-6-((1R,2S)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-3,4,5-triol 
• 115520-91-7 methyl 2,3,4,6,7,8-hexa-O-acetyl-β-L-threo-D-manno-octopyranoside 
• 5399-48-4 (2S,3S,4S,5S,6R)-2-Methoxy-6-((1R,2S)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-3,4,5-triol 
• 99202-72-9 1,2:3,4:6,7-tri-O-isopropylidene-α-D-threo-D-galacto-octodialdo-1,5-pyranose 
• 99202-72-9 (R)-2,2-Dimethyl-5-((3aR,5S,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-[1,3]dioxolane-4-carbaldehyde 
• 99202-70-7 methyl 1,2:3,4:6,7-tri-O-isopropylidene-β-L-erythro-D-galacto-octopyranuronate 
• 106256-20-6 1,2:3,4:6,7-tri-O-isopropylidene-α-D-threo-D-galacto-octopyranose 
• 69515-92-0 (Z)-6,7,8-trideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-oct-6-enopyranose 
• 71553-88-3 metrhyl (Z)-6,7-dideoxyl-1,2:3,4-di-O-isopropylidene-α-D-galacto-oct-5-enopyranuronate 

Downstream Products

• 27655-86-3 D-erythro-D-galacto-octitol 

Relevant academic research and scientific papers

A new total synthesis of D-threo-L-talo-Octose

A new approach to the total, asymmetric synthesis of D-threo-L-talo-octose ((-)-1) and its derivatives is presented. It is based on the chemoselective Wittig-Horner monoolefination of a 5-deoxy-D-ribo-hexodialdose derivative 4 obtained by selective reduction of (-)-5-deoxy-2,3-O-isopropylidene-β-D- ribo-hexofuranurono-6,1-lactone ((-)-3). Allylic bromination of the resulting methyl (E)-oct-6-enofuranuronate (+)-5 followed by intramolecular nucleophilic displacement of the so-obtained bromides gave a 13.3 :1 mixture of (-)-methyl (E)-1,4-anhydro-6,7-dideoxy-2,3-O-isopropylidene-β-L-talo-oct-6- enopyranuronate ((-)-8) and methyl (E)-1,4-anhydro-6,7-dideoxy-2,3-O- isopropylidene-α-D-allo-oct-6-enopyranuronate (9). The double hydroxylation of the enoate (-)-8 followed Kishi's rule and gave the corresponding D-threo-β-L-talo-octopyranuronate derivative (-)-11 with a good diastereoselectivity. Reduction of ester (-)-11 and deprotection led to pure (-)-1.

Higher-carbon Sugars. Part 12. The Synthesis of New Octitols from D-Glucose and D-Mannose via the Osmylation of Unsaturated Precursors

Catalytic osmylation of methyl (E)-2,3,4-tri-O-benzyl-6,7-dideoxy-α-D-gluco-oct-6-enopyranoside (8) produced a mixture of methyl 2,3,4-tri-O-benzyl-β-L-threo-D-gluco-octopyranoside (9) and the corresponding α-D-threo-D-gluco isomer (10) in the ratio ca. 3

Higher-carbon Sugars. Part 1. The Synthesis of Some Octose Sugars via the Osmylation of Unsaturated Precursors

The stereochemical outcome of the osmium tetraoxide oxidation of a number of unsaturated carbohydrate derivatives, including (E)- and (Z)-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-oct-6-enopyranose (6) and (9), methyl (Z)-6,7-dideoxy-1,2:3,4-di-