721391-22-6

Upstream product

• 114474-86-1 [2R,3S,4R,6S,1'R]-3,4-isopropylidenedioxy-2-[(1,2-isopropylidenedioxy)ethyl]tetrahydro-2H-pyran-6-carboxylic acid 
• 106174-63-4 methyl 2,6-anhydro-3-deoxy-D-glycero-D-talo-octonate 
• 256343-21-2 [2R,3R,4S,6S,1'R]-3,4:1',2'-diisopropylidene-6-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydroxy-2-(1,2-dihydroxyethyl)tetrahydro-2H-pyran 
• 171411-67-9 [2S,3R,4S,6S]-6-(tert-butyldiphenylsilyloxymethyl)-3-hydroxy-4-phenylsulfonyl-2-(2-thiopyridyl)tetrahydro-2H-pyran 
• 171411-70-4 [1S,3S,5S,6S]-3-(tert-butyldiphenylsilyloxymethyl)-9-oxo-5-phenylsulfonyl-2,7-dioxabicyclo[4.3.0]nonane 
• 256343-23-4 (3aS,5S,7S,7aS)-7-Benzenesulfonyl-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furo[3,2-b]pyran-3-one 
• 171411-65-7 [2S,4S]-2-(tert-butyldiphenylsilyloxymethyl)-4-phenylsulfonyl-3,4-dihydro-2H-pyran 
• 171411-71-5 [4S,6S,1'R]-2-(tert-butyldiphenylsilyloxymethyl)-6-(1,2-dihydroxyethyl)-3,6-dihydro-2H-pyran 
• 114474-75-8 2,6-anhydro-3-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-talo-octitol 
• 109150-74-5 methyl [2R,3S,4R,6S,1'R]-3,4-isopropylidenedioxy-2-[(1,2-isopropylidenedioxy)ethyl]tetrahydroo-2H-pyran-6-carboxylate 
• 107961-77-3 methyl 2,6-anhydro-3-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-octonate 
• 226226-37-5 C₂₆H₂₈O₉ 

Downstream Products

• 137040-53-0 (R)-2-((S)-2-{[(2S,4R,5R,6R)-6-((R)-1,2-Dihydroxy-ethyl)-4,5-dihydroxy-tetrahydro-pyran-2-carbonyl]-amino}-propionylamino)-pentanedioic acid dibenzyl ester 
• 137040-55-2 (R)-4-[(S)-5-Benzyloxycarbonylamino-1-((R)-1-benzyloxycarbonyl-ethylcarbamoyl)-pentylcarbamoyl]-2-((S)-2-{[(2S,4R,5R,6R)-6-((R)-1,2-dihydroxy-ethyl)-4,5-dihydroxy-tetrahydro-pyran-2-carbonyl]-amino}-propionylamino)-butyric acid benzyl ester 
• 137040-54-1 (S)-6-Benzyloxycarbonylamino-2-[(R)-4-benzyloxycarbonyl-4-((S)-2-{[(2S,4R,5R,6R)-6-((R)-1,2-dihydroxy-ethyl)-4,5-dihydroxy-tetrahydro-pyran-2-carbonyl]-amino}-propionylamino)-butyrylamino]-hexanoic acid benzyl ester 
• 137040-56-3 (S)-6-Benzyloxycarbonylamino-2-((R)-4-benzyloxycarbonyl-4-{[(2S,4R,5R,6R)-6-((R)-1,2-dihydroxy-ethyl)-4,5-dihydroxy-tetrahydro-pyran-2-carbonyl]-amino}-butyrylamino)-hexanoic acid benzyl ester 
• 137040-52-9 (R)-4-Carbamoyl-4-((S)-2-{[(2S,4R,5R,6R)-6-((R)-1,2-dihydroxy-ethyl)-4,5-dihydroxy-tetrahydro-pyran-2-carbonyl]-amino}-propionylamino)-butyric acid benzyl ester 

Relevant academic research and scientific papers

Template-directed intramolecular C-glycosidation. Formation of tetrahydrofurans and application to the synthesis of a higher-order sugar

Cation-mediated cyclisation reactions of silyl enol ether-containing thioglycosides give bicyclic ketotetrahydrofurans. Cyclisation of an analogous 3-phenyl-2-propenyl ether-containing substrate gives an intermediate in the total synthesis of the higher-order sugar 2,3-dideoxy-D- manno-2-octulopyranosonic acid.

Total synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO) and 2-deoxy-β-KDO

(equation presented) Total syntheses of KDO and 2-deoxy-β-KDO are reported. The C2-symmetric dienediol 4 was desymmetrized by conversion to its corresponding 1,4-dioxanone 5. Ireland-Claisen rearrangement of 5 provided the 6-vinyldihydropyran-2-carboxylate template 6. Double-Sharpless asymmetric dihydroxylation gave the tetraol 7a, which was converted to KDO and 2-deoxy-β-KDO using methods similar to those previously reported. This synthetic scheme provides a flexible route to KDO and KDO analogues.

Template-directed intramolecular C-glycosidation. Total synthesis of 2,3-dideoxy-D-manno-2-octulopyranosonic acid

The total synthesis of the KDO-inhibitor 2,3-dideoxy-D-manno-2-octulopyranosonic acid (2-deoxy-KDO) starting from TBDPS-protected (S)-glycidol and 3,3-dimethoxy-1-(phenylsulfonyl)-propane is described. The key steps are silver(I) trifluoromethylsulfonate-