72002-52-9

Upstream product

• 85439-71-0 methyl-3,4-anhydro-2,6-didesoxy-β-L-lyxo-hexopyranoside 
• 19131-11-4 methyl-2,6-didesoxy-β-L-arabino-hexopyranoside 
• 72062-86-3 methyl-3,4-di-O-acetyl-2,6-didesoxy-β-L-arabino-hexopyranoside 
• 85373-07-5 methyl-3-O-benzoyl-2,6-didesoxy-β-L-arabino-hexopyranoside 
• 85373-08-6 methyl-3-O-benzoyl-2,6-didesoxy-4-O-methylsulfonyl-β-L-arabino-hexopyranoside 
• 34819-86-8 3,4-di-O-acetyl-6-deoxy-L-glucal 
• 75412-26-9 methyl 3-azido-6-bromo-2,3,6-tridesoxy-α-D-ribohexopyranoside 
• 66409-28-7 (1R,2R,4S,6R)-4-Methoxy-2-methyl-3,7-dioxa-bicyclo[4.1.0]heptane 
• 72062-88-5 Benzoic acid (2R,3R,4R,6S)-4-methanesulfonyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester 
• 6600-11-9 methyl 4,6-O-benzylidene-2-deoxy-3-O-mesyl-α-D-altropyranoside 
• 72062-67-0 Benzoic acid (2S,3R,4S,6S)-2-bromomethyl-4-methanesulfonyloxy-6-methoxy-tetrahydro-pyran-3-yl ester 
• 18944-96-2 methyl 4-O-benzoyl-2,6-dideoxy-α-D-arabino-hexopyranoside 
• 18933-64-7 Benzoic acid (2S,3S,4R,6S)-2-bromomethyl-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl ester 
• 13322-79-7 (2R,3S,4R,6S)-6-Methoxy-2-methyl-tetrahydro-pyran-3,4-diol 

Downstream Products

• 72075-75-3 (2R,3R,4R,6S)-4-Azido-6-methoxy-2-methyl-tetrahydro-pyran-3-ol 
• 149055-63-0 3-Azido-1,4-di-O-(p-nitrobenzoyl)-2,3,6-trideoxy-α,β-L-arabino-hexopyranose 

Relevant academic research and scientific papers

Hydrogen-Bonding-Assisted Exogenous Nucleophilic Reagent Effect for β-Selective Glycosylation of Rare 3-Amino Sugars

Challenges for stereoselective glycosylation of deoxy sugars are notorious in carbohydrate chemistry. We herein report a novel strategy for the construction of the less investigated β-glycosidic bonds of 3,5-trans-3-amino-2,3,6-trideoxy sugars (3,5-trans-3-ADSs), which constitute the core structure of several biologically important antibiotics. Current protocol leverages a C-3 axial sulfonamide group in 3,5-trans-3-ADSs as a hydrogen-bond (H-bond) donor and repurposes substoichiometric phosphine oxide as an exogenous nucleophilic reagent (exNu) to establish an intramolecular H-bond between the former and the derived α-oxyphosphonium ion. This pivotal interaction stabilizes the α-face-covered intermediate to inhibit the formation of the more reactive β-intermediate, thereby yielding reversed β-selectivity, which is unconventional for an exNu-mediated glycosylation system. A wide range of substrates was accommodated, and good to excellent β-selectivities were ensured by this H-bonding-assisted exNu effect. The robustness of the current strategy was further attested by the architectural modification of natural products and drugs containing 3,5-trans-3-ADSs, as well as the synthesis of a trisaccharide unit in avidinorubicin.

C-glycosylation of oxygenated naphthols with 3-dimethylamino- 2,3,6-trideoxy-L-arabino-hexopyranose and 3-azido- 2,3,6-trideoxy-D-arabino-hexopyranose

In connection with studies directed towards the synthesis of the pyranonaphthoquinone antibiotic medermycin, C-aryl glycosides were prepared by C-glycosylation of naphthols with glycosyl donors. Boron trifluoride diethyl etherate proved to be a suitable Lewis acid to promote the C-glycosylation, and use of the azido glycosyl donor proved more successful than using the dimethylamino glycosyl donor. 5-Hydroxy-1,4-dimethoxynaphthalene underwent facile C-glycosylation with two particular glycosyl donors, whereas 3-bromo-5-hydroxy-1,4-dimethoxynaphthalene was not an effective coupling partner with the same glycosyl donors. These studies indicate that subtle steric and electronic effects need to be considered in order to fine-tune C-glycosylations when using highly functionalized glycosyl donors.

Addition of Hydrazoique Acid to Pseudoglycals Stereoselective Synthesis of L-Acosamine and L-Daunosamine

Methyl and benzyl glycosides and glycal of L-acosamine (3-amino-2,3,6 trideoxy-L-arabino-hexose) have been stereoselectively prepared via 1,4-addition of hydrazoic acid to L-erythro-hex-2-enopyranose as a key step.Inversion of the C-4 configuration of met

Stereocontrolled Route to 3-Amino-2,3,6-trideoxy-hexopyranoses. K-10 Montmorillonite as a Glycosidation Reagent for Acosaminide Synthesis

A stereoselective synthesis of methyl .(or benzyl) 3-azido-2,3,6-trideoxy-α-L-arabino-hexopyranoside from di-O-acetyl-L-rhamnal is reported; it proceeds via addition of hydrazoic acid to a hex-2-enopyranose, followed by acetylation and glycosidation with

SYNTHESE ET REACTIVITE VIS-A-VIS DE REACTIFS NUCLEOPHILES DES METHYL-3,4-ANHYDRO-2,6-DIDESOXY-α- ET -β-L-lyxo- ET -ribo-HEXOPYRANOSIDES

The ring-opening reactions of methyl 3,4-anhydro-2,6-dideoxy-α- and -β-L-lyxo- and -ribo-hexopyranosides with sodium azide, ammonia, methyl- and dimethylamine, and sodium methoxide were studied.Regioselectivity is explained in terms of steric and conforma