63053-84-9

Upstream product

• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 538-75-0 dicyclohexyl-carbodiimide 
• 65-85-0 benzoic acid 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 98-88-4 benzoyl chloride 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 
• 122128-11-4 Thiobenzoic acid S-(3-nitro-pyridin-2-yl) ester 
• 455-32-3 benzoyl fluoride 

Downstream Products

• 21056-52-0 Benzoic acid (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl ester 
• 6207-45-0 2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran 
• 201593-51-3 5,5-Dimethyl-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylsulfanyl)-[1,3,2]dioxaphosphinane 2-oxide 
• 201593-55-7 5,5-Dimethyl-2-thioxo-2-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosylthio)-1,3,2-dioxaphosphorinane 

Relevant academic research and scientific papers

Glycosyl ortho-Methoxybenzoates: Catalytically Activated Glycosyl Donors with an Easily Removable and Recyclable Leaving Group

We describe the β-ortho-methoxybenzoate as a shelf stable and practical C-1 nucleofuge for catalytic chemical glycosylation in which the benzoic acid by-product can be easily removed, reisolated, and potentially recycled after the glycosylation reaction. This new type of glycosyl donor can be efficiently activated by a range of promoters, including Bi(OTf)3, Fe(OTf)3, TMSOTf (TMS = trimethylsilyl), and triflic acid, with low (10 mol-%) catalyst loadings. The donor shows higher reactivity than analogous benzoate, p-methoxybenzoate and p-cyano-o-methoxybenzoate donors. In glycosylation reactions with o-methoxybenzoate donors, the yields of disaccharide products were good to excellent for various glycosyl acceptors, including a carbohydrate-based secondary alcohol. Furthermore, β-selective mannosylation was achieved with a Crich-type donor at 0 °C to ambient temperature, without donor preactivation. The donor was also used for the first step of a one-pot two-step glycosylation to obtain a trisaccharide; the second coupling involved activation of a thioglycoside with NIS/TMSOTf (NIS = N-iodosuccinimide). We believe that this offers a good alternative to current protocols.

Combined Lewis acid and Br?nsted acid-mediated reactivity of glycosyl trichloroacetimidate donors

Biomimetic conditions for a synthetic glycosylation reaction, inspired by the highly conserved functionality of carbohydrate active enzymes, were explored. At the outset, we sought to generate proof of principle for this approach to developing catalytic systems for glycosylation. However, control reactions and subsequent kinetic studies showed that a stoichiometric, irreversible reaction of the catalyst and glycosyl donor was occurring, with a remarkable rate variance depending upon the structure of the carboxylic acid. It was subsequently found that a combination of Br?nsted acid (carboxylic acid) and Lewis acid (MgBr2) was unique in catalyzing the desired glycosylation reaction. Thus, it was concluded that the two acids act synergistically to catalyze the desired transformation. The role of the catalytic components was tested with a number of control reactions and based on these studies a mechanism is proposed herein.

Simple Synthesis of β-D-Glucosyl Esters

Acylation of 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose (1) with benzoyl chloride and triethylamine was found to give 1-O-benzoyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose (2) and 1-O-benzoyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranose (3) in a ratio of 2:9 whi

A CONVENIENT STEREOSELECTIVE SYNTHESIS OF α-GLYCOSYL ESTERS

The anomeric hydroxyl group of 2,3,4,6-tetra-O-benzyl-D-glucopyranose was esterified by reaction of the derived anomeric alkoxide with 2-acylthio-3-nitropyridines at -78 deg C.The resultant esters were obtained with high anomeric diastereoselectivity (α:β

AN EFFICIENT SYNTHESIS OF GLYCOSYL ESTERS EXPLOITING THE MITSUNOBU REACTION.

The anomeric hydroxyl group of various pyranose hemiacetals can be esterified with inversion of configuration, conveniently, mildly and on large-scale using triphenylphosphine (TPP), with either diisopropylazodicarboxylate (DIAD) or diethylazodicarboxylat

SYNTHESES OF 1-O-ACYLALDOSE DERIVATIVES via THE CORRESPONDING O-GLYCOSYLPSEUDOUREAS

A series of 1-O-acylaldose derivatives was prepared in good yield throught the reaction of 1,3-dialkyl-O-glycosylpseudoureas with carboxylic acids.

STEREOSELECTIVE SYNTHESIS OF 1-O-ACYL-D-GLUCOPYRANOSE FROM 1-HYDROXY SUGAR AND ACYL FLUORIDES BY THE PROMOTION OF CESIUM FLUORIDE

In the presence of cesium fluoride, the reaction of 2,3,4,6-tetra-O-benzyl-D-glucopyranose with acyl fluorides affords the corresponding glucosyl esters in good yields under essentially neutral condition.The α/β ratio of produced glucosyl esters is greatl