86117-82-0

Upstream product

• 90695-22-0 (1R)-(+)-(1,3,5/2,4)-2,3,4,5-tetrahydroxycyclohexane-1-methanol penta-acetate 
• 90695-20-8 (1S)-2-exo,3-endo-diacetoxy-5-endo-acetoxymethyl-7-oxabicyclo<2.2.1.>heptane 
• 5040-08-4 1,2-O-isopropylidene-α-D-xylo-5-hexulofuranurono-6,3-lactone 
• 152434-60-1 (3aR,3bS,6S,6aS,7aR)-6-Hydroxy-2,2-dimethyl-6-nitromethyl-tetrahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-5-one 
• 152434-63-4 C₂₄H₂₅NO₉ 
• 152434-61-2 (3aR,3bS,6S,6aS,7aR)-6-(2-Ethoxy-ethoxy)-2,2-dimethyl-6-nitromethyl-tetrahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-5-one 
• 10226-79-6 Pseudo-β-DL-gulopyranose-pentaacetat; DL-1-Acetoxymethyl-2,3,4,5-tetraacetoxy-cyclohexan 
• 64589-25-9 exo-2, endo-3-diacetoxy-endo-5-acetoxymethyl-7-oxabicyclo[2.2.1]heptane 
• 90760-56-8 (-)-7-endo-oxabicyclo<2.2.1>hept-5-ene-2-carboxylic acid 
• 74517-36-5 tetra-O-acetyl-(1,3,5/2,4)-2-bromo-5-hydroxymethyl-1,3,4-cyclohexanetriol 
• 69982-68-9 endo-3-acetoxy-endo-5-acetoxymethyl-exo-2-bromo-7-oxabicyclo<2.2.1>heptane 
• 74517-36-5 tetra-O-acetyl-(1,2/3,4,5)-2-bromo-5-hydroxymethyl-1,3,4-cyclohexanetriol 
• 97321-78-3 2,3:4,7-di-O-isopropylidene-(2,3,5/4)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexanone 
• 64716-98-9 (1RS,2RS,7RS,9SR,10RS)-4,4,12,12-tetramethyl-3,5,11,13-tetraoxatricyclo<8.3.0.0^2,7>-tridecan-9-ol 

Downstream Products

• 89859-82-5 (2R,3S,4R,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexanone 
• 10226-73-0 DL-(1,5/2,3,4)-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol 
• 10226-79-6 DL-(1,5/2,3,4)-5-acetoxymethyl-1,2,3,4-tetra-acetoxycyclohexane 
• 10226-73-0 (1R,2R,3S,4R,5R)-5-Hydroxymethyl-cyclohexane-1,2,3,4-tetraol 
• 64714-19-8 Toluene-4-sulfonic acid (3aR,4R,5aS,9aS,9bR)-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-yl ester 
• 10226-79-6 DL-(1,2,3,5/4)-5-acethoxymethyl-1,2,3,4-tetra-O-acetyl-1,2,3,4-cyclohexanetetrol 
• 117938-24-6 (2R,4aR,6R,7S,8S,8aR)-6,7,8-Tris-benzyloxy-2-phenyl-hexahydro-benzo[1,3]dioxine 
• 117902-50-8 (1RS,3RS,6RS,8RS,9SR,10SR)-8,9,10-trihydroxy-3-phenyl-2,4-dioxabicyclo<4.4.0>decane 
• 117938-24-6 (4aR,6S,7S,8S,8aR)-6,7,8-Tris-benzyloxy-2-phenyl-hexahydro-benzo[1,3]dioxine 
• 134428-47-0 6-O-acetyl-1,2,3-tri-O-benzyl-5a-carba-α-DL-glucopyranose 
• 125258-11-9 DL-(1,2,4/3,5)-1,2,3-tri-O-benzyl-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol 
• 134428-50-5 6-O-acetyl-1,2,3-tri-O-benzyl-4-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-5a-carba-α-L-glucopyranose 
• 134428-50-5 6-O-acetyl-1,2,3-tri-O-benzyl-4-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-5a-carba-α-D-glucopyranose 
• 134428-49-2 6-O-acetyl-1,2,3-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5a-carba-α-L-glucopyranose 

Relevant academic research and scientific papers

TOTAL SYNTHESIS AND ABSOLUTE CONFIGURATION OF (+)-(1,2,3/4,5)-2,3,4,5-TETRAHYDROXY-1-CYCLOHEXANEMETHANOL

The title branched-chain cyclitol has been synthesized from chiral 7 endo-oxabicyclohept-5-ene-2-carboxylic acid, the absolute configuration of which was established on the basis of X-ray analysis of crystalline bromolactone derived from it.From th

On the Origin of Regioselectivity in Palladium-Catalyzed Oxidation of Glucosides

The palladium-catalyzed oxidation of glucopyranosides has been investigated using relativistic density functional theory (DFT) at ZORA-BLYP?D3(BJ)/TZ2P. The complete Gibbs free energy profiles for the oxidation of secondary hydroxy groups at C2, C3, and C

Synthesis of 5a,5a′-dicarba-D-glucobioses from conformationally restricted carbaglucosyl triflates using SN2-type inversion with carbaglucosyl nucleophiles

Novel carbohydrate mimics were designed which contain two 5a-carba-D-glucose residues, one each at reducing and nonreducing end, and thus these mimics are 5a,5a′-dicarba-D-glucobioses. Dicarbadisaccharides have attractive features such as stability agains

Synthesis of some carbahexopyranoses using Mn/CrCl3 mediated domino reactions and ring closing metathesis

An efficient and common method for the synthesis of 5a-carba-α-D-mannopyranose 5, 5a-carba-β-D-mannopyranose 6, (+) methyl shikimate 9, (+) methyl-5-epi-shikimate 10, validamine analogue 15 and valiolamine analogue 16 from D-mannose, formal synthesis of T

Synthesis of an ether-linked alkyl 5a-carba-β-D-glucoside, a 5a-carba-β-D-galactoside, a 2-acetamido-2-deoxy-5a-carba-β-D-glucoside, and an alkyl 5a′-carba-β-lactoside

For the purpose of providing biologically stable building blocks for the biocombinatorial synthesis using a living cell, some ether-linked alkyl 5a-carba-β-D-glycoside primers were prepared. The key step of the synthesis was coupling of 1-bromo-n-alkanes with the 1-OH unprotected derivatives of 5a-carba-sugar analogues of D-glucose, D-galactose, and 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine), in DMF in the presence of sodium hydride. Alternatively, alkyl carba-lactoside was synthesized by incorporation of a 5a-carba-β-D-galactose residue into the 4-position of dodecyl β-D-glucopyranoside. A strong and specific inhibition of β-galactosidase (Ki 0.67 μM, bovine liver) was found for dodecyl 5a-carba-β-D-galactopyranoside.

A norbornyl route to cyclohexitols: Structural diversity in fragmentation through functional group switching. Synthesis of α- and β- galactose, α-talose and α-fucopyranose carbasugars

A novel fragmentation sequence has been executed within the norbornane system, involving C1-C7 bond scission, to extract a versatile, highly functionalized cyclohexanoid moiety. Its further evolution towards a range-of carbasugars is described. (C) 2000 Elsevier Science Ltd.

Stereoselective conversion of D-glucuronolactone into pseudosugar: Synthesis of pseudo-α-D-glucopyranose, pseudo-β-D-glucopyranose, and validamine

Two optically active pseudo-sugars, pseudo-α-D-glucopyranose (12) and pseudo-β-D-glucopyranose (13), were synthesized from D-glucuronolactone in favorable overall yields by using a stereoselective nitromethane addition reaction and a reductive elimination of an ethoxyethoxyl moiety with NaBH4 as key steps. Furthermore, a biologically active pseudo-aminosguar, validamine (18) was efficiently synthesized via a substitution reaction for an acetoxyl group at the β-position of nitro group in a nitrocyclitol derivative (14) which was prepared from a synthetic intermediate (9) of pseudo-d-glucopyranoses (12,13).

Syntheses of pseudo-α-D-glucopyranose, pseudo-β-D-glucopyranose, and validamine from D-glucuronolactone

Using a stereoselective nitromethane addition and a reductive elimination of an ethoxyethoxyl moiety with NaBH4 as key steps, two optically active pseudo-sugars, pseudo-α-D-glucopyranose and pseudo-β-D-glucopyranose, were synthesized from D-glucuronolactone in favorable overall yield. Furthermore, a biologically active pseudo-aminosugar, validamine, was synthesized via a substitution reaction for an acetoxyl group at the β-position of the nitro group in the nitrocyclitol derivative which was prepared from a synthetic intermediate of pseudo-D-glucopyranose.

Strain-Directed Bridge Cleavage of (Phenylsulfonyl)-7-oxabicycloheptane Derivatives: Application to the Total Synthesis of Carba-α-DL-glucopyranose

New methodology to prepare highly oxygenated cyclohexenylsulfones by regioselective β-elimination of (phenylsulfonyl)-7-oxabicycloheptane derivatives has been developed, and its application to the total synthesis of carba-α-DL-glucopyranose is desc

Cyclitol Reactions, XIII.- Synthesis of Pseudosugars from D-Glucose by Intramolecular Horner-Emmons Olefination

The reaction of the aldehyde 3, prepared from D-glucose diethyl dithioacetal via 1 and 2, with lithium dimethyl methylphosphonat yields the adduct 4.Conversion of 4 into 9 followed by Swern oxidation results in the enone 6.Hydrogenation of 6 leads to pseu