37073-70-4

Upstream product

• 582-52-5 1,2:5,6-diacetone-D-glucose 
• 101475-83-6 3-O-benzyl-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 
• 76-83-5 trityl chloride 
• 42926-89-6 1,2-O-isopropylidene-3-O-benzyl-α-D-glucofuranose 
• 100-39-0 benzyl bromide 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 76-84-6 triphenylmethyl alcohol 

Downstream Products

• 117383-74-1 5-azido-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-6-O-trityl-β-L-idofuranose 
• 117383-73-0 N-[(S)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-trityloxy-ethyl]-2,2,2-trifluoro-acetamide 
• 1380315-48-9 3-O-benzyl-6-O-(2-bromomethylbenzyl)-5-O-(4-methoxybenzyl)-1,2-O-isopropylidene-α-D-glucofuranose 
• 1380315-49-0 6-O-(2-azidomethylbenzyl)-3-O-benzyl-5-O-(4-methoxybenzyl)-1,2-O-isopropylidene-α-D-glucofuranose 
• 1380315-50-3 C₆₈H₇₃N₃O₁₂S 
• 1380315-51-4 C₆₀H₆₅N₃O₁₁S 
• 1380315-52-5 3-O-benzyl-6-O-(3-bromomethylbenzyl)-5-O-(4-methoxybenzyl)-1,2-O-isopropylidene-α-D-glucofuranose 
• 1380315-53-6 6-O-(3-azidomethylbenzyl)-3-O-benzyl-5-O-(4-methoxybenzyl)-1,2-O-isopropylidene-α-D-glucofuranose 
• 1380315-54-7 C₆₈H₇₃N₃O₁₂S 
• 1380315-55-8 C₆₀H₆₅N₃O₁₁S 
• 222844-98-6 3-O-benzyl-5-O-(4-methoxybenzyl)-1,2-O-isopropylidene-α-D-glucofuranose 
• 1380315-47-8 3-O-benzyl-5-O-(4-methoxybenzyl)-6-O-triphenylmethyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 1402436-23-0 6-benzyloxy-2,2-dimethyl-5-(1-prop-2-ynyloxy-2-trityloxyethyl)tetrahydrofuro[2,3-d][1,3]dioxole 
• 1402436-49-0 C₂₆H₂₈O₆ 

Relevant academic research and scientific papers

Synthesis of β-lactams: Via diastereoselective, intramolecular Kinugasa reactions

Intramolecular Kinugasa reactions on in situ generated carbohydrate-derived alkynylnitrones are described. The effects of the length of chains, their mutual configuration, influence of experimental conditions on product distribution and feasibility of the

Synthesis of carbohydrate fused chiral macrocyclic benzolactones through Sonogashira reaction

Synthesis of 10-, 11- and 12-membered chiral benzolactones fused to furanose/pyranose sugars has been achieved in good to excellent yields using an intramolecular Sonogashira reaction. Positions 1-2, 3-5, 3-6 and 5-6 of sugar were utilized for the constru

Disaccharide-containing macrocycles by click chemistry and intramolecular glycosylation

In this study o- and m-xylylene moieties in combination with a triazolylmethyl moiety have been successfully employed as a relatively rigid spacer system in intramolecular glycosylation reactions. Phenyl 3,4,6-tri-O-benzyl-2-O-propargyl-1-thio-D-glucopyra

Intramolecular base-free sonogashira reaction for the synthesis of benzannulated chiral macrocycles embedded in carbohydrate templates

A base-free, intramolecular Sonogashira reaction-based general approach has been established for the diversity-oriented synthesis (DOS) of fused bi- and tricyclic systems containing benzannulated, 10- to 13-membered chiral macrocycles embedded in carbohydrate templates. Macrocycles with different ring sizes have been prepared by pre-designing the chiral building blocks. Base-sensitive groups like acetyl and TBDPS survived the reaction conditions. Copyright

Tris(pentafluorophenyl)borane: a mild and efficient catalyst for the chemoselective tritylation of alcohols

An efficient acid-catalyzed protection of alcohols as trityl ethers is described using triphenylmethanol in the presence of tris(pentafluorophenyl)borane (3 mol %) in dichloromethane at room temperature. The chemoselectivity of this protocol is demonstrat

SYNTHESIS OF HEPARIN FRAGMENTS. A CHEMICAL SYNTHESIS OF THE TRISACCHARIDE O-(2-DEOXY-2-SULFAMIDO-3,6-DI-O-SULFO-α-D-GLUCOPYRANOSYL)-(1->4)-O-(2-O-SULFO-α-L-IDOPYRANOSYL-URONIC ACID)-(1->4)-2-DEOXY-2-SULFAMIDO-6-O-SULFO-D-GLUCOPYRANOSE HEPTASODIUM SALT

Known 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose was first converted into methyl 3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranuronate.Acid hydrolysis, followed by acetylation and treatment with titanium tetrabromide, gave methyl (2,4-di-O-acetyl-3-O-benzyl-α-L-idopyranosyl bromide)uronate, which was immediately transformed into methyl 4-O-acetyl-3-O-benzyl-β-L-idopyranuronate 1,2-(tert-butyl orthoacetate).A two-step replacement of the 4-O-acetyl by a 4-O-chloroacetyl group gave the key derivative, crystalline methyl 3-O-benzyl-4-O-chloroacetyl-β-L-idopyranuronate 1,2-(tert-butyl orthoacetate).Condensation of this orthoester with an excess of crystalline benzyl 6-O-acetyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside in chlorobenzene in the presence of 2,6-dimethylpyridinium perchlorate gave crystalline benzyl 6-O-acetyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-α-D-glucopyranoside in 40 percent yield.O-Demonochloroacetylation, followed by condensation with known 3,6-di-O-acetyl-2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl bromide in dichloromethane in the presence of 2,4,6-trimethylpyridine, silver triflate, and molecular sieve provided benzyl O-(3,6-di-O-acetyl-2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside in 88 percent yield.O-Deacetylation with sodium hydroxide, followed successively by O-sulfation in N,N-dimethylformamide in the presence of sulfur trioxide-trimethylamine complex, catalytic hydrogenolysis, and N-sulfation in water with the same sulfating agent, gave the heptasodium salt of O-(2-deoxy-2-sulfamido-3,6-di-O-sulfo-α-D-glucopyranosyl)-(1->4)-O-(2-O-sulfo-α-L-idopyranosyluronic acid)-(1->4)-2-deoxy-2-sulfamido-6-O-sulfo-D-glucopyranose.This trisaccharide, which is a fragment of the minimal antithrombin III-binding region in heparin, neither binds to antithrombin III nor induces anti-Xa activity.