51213-03-7

Upstream product

• 76-83-5 trityl chloride 
• 43138-65-4 1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 139710-09-1 5-O-Acetyl-1,2-O-isopropylidene-3-O-methyl-6-O-triphenylmethyl-α-D-glucopyranose 
• 24807-96-3 3-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 172744-72-8 1,2-isopropylidene-5-O-(2-methoxyethyl)-3-O-methyl-6-O-trityl-α-D-glucofuranose 
• 139710-09-1 5-O-Acetyl-1,2-O-isopropylidene-3-O-methyl-6-O-triphenylmethyl-α-D-glucopyranose 
• 83021-84-5 5-O-benzyl-1,2-O-isopropylidene-3-O-methyl-6-O-triphenylmethyl-D-glucofuranose 
• 89821-69-2 5-O-allyl-1,2-isopropylidene-3-O-methyl-6-O-trityl-α-D-glucofuranose 
• 51173-26-3 (3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-5-1-[(trityloxy)methyl]vinylperhydrofuro[2,3-d][1,3]dioxole 
• 1414099-95-8 tert-butyl N-[2(R)-2-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethylperhydrofuro[2,3-d]-[1,3]dioxol-5-yl]-3-methoxypropyl]carbamate 
• 1414099-90-3 tert-butyl N-[2(R)-2-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethylperhydrofuro[2,3-d]-[1,3]dioxol-5-yl]-3-hydroxypropyl]carbamate 
• 1414099-85-6 tert-butyl N-[2(S)-2-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl]-3-hydroxypropyl]carbamate 
• 1414099-80-1 tert-butyl N-[2(S)-2-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethylperhydrofuro[2,3-d]-[1,3]dioxol-5-yl]-3-methoxypropyl]carbamate 
• 51173-23-0 1-((3aR,5S,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-trityloxy-ethanone 
• 83021-87-8 5-O-benzyl-3-deoxy-D-erythro-hexonic acid, cyclohexylammonium salt 
• 473734-82-6 6-O-(p-tert-butyldimethylsilyloxyphenylsulfonyl)-1,2-O-isopropylidene-3-O-methyl-5-O-(prop-1'-enyl)-α-D-glucofuranose 

Relevant academic research and scientific papers

Enhanced reactivity of secondary hydroxyl groups in the O-alkylation of carbohydrate-related primary-secondary vic-glycols. Regioselective 2-O-benzylation of 1,3:2,4-di-O-ethylidene-D-glucitol

Partial O-alkylation of 1,3:2,4-di-O-ethylidene-D-glucitol (1a), 1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose (1b), and R-(+)-1-O-benzylglycerol (1c) with benzyl chloride in a KOH/DMSO system results in products of monoalkylation at the secondary (4a-c) and at the primary hydroxyl (2a-c) in ratios of over 95:5 (a), ca. 2:1 (b), and ca. 1:1 (c), whereas (+/-)propane-1,2-diol (1d) gives only the product of 1-O-benzylation (2d).A qualitatively similar result is observed upon O-alkylation of diols (1a-e) with 2-methoxyethanol tosylate.

Synthesis of C-linked carbo-β2-amino acids and β2-peptides: Design of new motifs for left-handed 12/10- and 10/12-mixed helices

C-linked carbo-β2-amino acids (β2-Caa), a new class of β-amino acid with a carbohydrate side chain having d-xylo configuration, were prepared from d-glucose. The main idea behind the design of the new β-amino acids was to move the steric strain of the bulky carbohydrate side chain from the Cβ- to the Cα-carbon atom and to explore its influence on the folding propensities in peptides with alternating (R)- and (S)-β2-Caas. The tetra- and hexapeptides derived were studied employing NMR (in CDCl3), CD, and molecular dynamics simulations. The β2-peptides of the present study form left-handed 12/10- and 10/12-mixed helices independent of the order of the alternating chiral amino acids in the sequence and result in a new motif. These results differ from earlier findings on β3-peptides of the same design, containing a carbohydrate side chain with d-xylo configuration, which form exclusively right-handed 12/10-mixed helices. Quantum chemical calculations employing ab initio MO theory suggest the side chain chirality as an important factor for the observed definite left- or right-handedness of the helices in the β2- and β3-peptides.

Enzymic deacetylation of derivatives of 1,2-O-isopropylidene-α-D-hexofuranoses

Enzymically catalysed, partial deacetylation of the 5,6-diacetates of 3-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose and 1,2-O-isopropylidene-α-D-gluco- and -allo-furanose with different substituents at C-3(OAc, OMe, NHAc) gives the 5-acetate, wich mi

Synthesis and Behaviour under Acidic Conditions of 2-Deoxy-D-arabino-hexopyranose and 3-Deoxy-2-ketoaldonic Acids Bearing O-Phosphono or O-Glucosyl Substituents at Position β to the Carbonyl Function

Methyl 4-O-phosphono- and 4-O-(β-D-glucopyranosyl)-3-deoxy-β-D-erythro-2-hexulopyranosidonic acids, and 3-O-phosphono-, and 3-O-(β-D-glucopyranosyl)-2-deoxy-α-D-arabino-hexopyranoses have been synthesised and their behaviour in acidic media examined.At 10