38430-69-2

Upstream product

• 3947-62-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 65-85-0 benzoic acid 
• 407-25-0 trifluoroacetic anhydride 
• 108-24-7 acetic anhydride 
• 1053622-46-0 O³,O⁴,O⁶-Triacetyl-O¹-benzoyl-β-D-glucopyranose 
• 81342-44-1 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 93-97-0 benzoic acid anhydride 
• 3254-17-9 3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-α-D-glucopyranose 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 78942-86-6 2,3,4,6-tetra-O-acetyl-1-O-trifluoroacetyl-α-D-glucopyranose 
• 21056-52-0 Benzoic acid (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl ester 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 439-03-2 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose 
• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 

Relevant academic research and scientific papers

Improved synthesis of 1-O-acyl-β-D-glucopyranose tetraacetates

An improved synthesis of 1-O-acyl glucosyl esters that avoids the use of expensive Ag reagents as well as the hydrolysis of unstable glucosyl bromides is reported. Notably, β-configuration products were obtained exclusively in good yields.

Reversing Reactivity: Stereoselective Desulfurative 1,2- trans- O-Glycosylation of Anomeric Thiosugars with Carboxylic Acids under Copper or Cobalt Catalysis

We have discovered a new mode of reactivity of 1-thiosugars in the presence of Cu(II) or Co(II) for a stereoselective O-glycosylation reaction. The process involves the use of a catalytic amount of Cu(acac)2 or Co(acac)2 and Ag2CO3 as an oxidant in α,α,α-trifluorotoluene. Moreover, this protocol turned out to have a broad scope, allowing the preparation of a wide range of complex substituted O-glycoside esters in good to excellent yields with an exclusive 1,2-trans-selectivity. The late-stage modification of pharmaceuticals by this method was also demonstrated. To obtain a closer insight into the reaction mechanism, cyclic voltammetry was performed.

Synthesis of various β-D-glucopyranosyl and β-Dxylopyranosyl hydroxybenzoates and evaluation of their antioxidant activities

Various β-D-glucopyranosyl and β-Dxylopyranosyl hydroxybenzoates were efficiently prepared from 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (TAGB) or 2,3,4-tri-O-acetyl-α-D-xylopyranosyl bromide (TAXB), respectively, by amine-promoted glycosylation.

Synthesis of some monosaccharide-related ester derivatives as insecticidal and acaricidal agents

To develop natural-product-based pesticidal agents, a series of monosaccharide-related ester derivatives (17a–q and 18a–f), glucose (xylose)-piperic acid/piperic acid-like conjugates, were synthesized. Three-dimensional structures of compounds 17b, 17g, 17h, and 17n were unambiguously determined by single-crystal X-ray diffraction. Especially compounds 18e and 18f exhibited the most potent insecticidal and acaricidal activities against Mythimna separata and Tetranychus cinnabarinus. Their structure-activity relationships were also discussed.

Polyvinyl trisulfonate ethylamine based solid acid catalyst for the efficient glycosylation of sugars under solvent free conditions

Heterogeneous Bronsted solid acid catalysts have the potential to decrease the environmental impact related to chemical production. Herein, we have synthesized polyvinyl bound trisulfonate ethylamine chloride (PV-THEAC) and polyvinyl bound disulfonate ethylamine (PV-DSEA) as Bronsted solid acid catalysts which exhibited effective catalytic activity for acid catalyzed glycosylation reactions with sugar derivatives. In particular, 0.3 equiv. of the PV-THEAC catalyst was found to be the most efficient and a reusable catalyst for glycosylation reactions. A high density of the trisulfonic group (-OSO3H) contributed to the excellent catalytic activity during glycosylation. Moreover, glycosylation reactions with d-mannose, d-xylose and d-glucose have been studied with alcohol. Remarkable acceleration of the glycosylation reaction using a glycosyltrichloroacetimidate donor was obtained with the selective production of β-glycoside.

Highly efficient β-glucosylation of the acidic hydroxyl groups, phenol and carboxylic acid, with an peracetylated glucosyl fluoride using a combination of BF3·Et2O and DTBMP as a promoter

A combination of BF3·Et2O and DTBMP was established to be an efficient promoter of β-glucosylation of both phenols and carboxylic acids with a peracetylated glucosyl fluoride (2). This new method achieved remarkably high yields and β

Phyllanthoside-Phyllanthostatin Synthetic Studies. 8. Total Synthesis of (+)-Phyllanthoside. Development of the Mitsunobu Glycosyl Ester Protocol

The first total syntheses of the antineoplastic glycoside (+)-phyllanthoside (1) and the parent disaccharide (-)-phyllanthose (5) have been achieved. Stereoselective Koenigs-Knorr coupling of two 6-deoxyglucose derivatives, bromide 54 and alcohol 55, generated the uncommon 1′ → 2β glycosidic linkage of (-)-phyllanthose. A stereochemically convergent Mitsunobu reaction of protected disaccharide 87 with aglycon carboxylic acid 80, prepared via asymmetric synthesis, then led to 1 of high enantiomeric purity. The Mitsunobu procedure comprises an efficient general method for stereospecific assembly of β-glycosyl esters.

Studies of Carbohydrates IV. A Novel Highly Stereoselective Synthesis of 1-O-Acyl-β-D-glucopyranose Tetraacetates via the Glucosyl Trifluoroacetate

2,3,4,6-Tetra-acetyl-glucose (1) reacted with trifluoroacetic anhydride to give good yield of 2,3,4,6-tetra-O-acetyl-1-α-O-trifluoroacetyl-α-D-glucopyranose (2) wich was converted into corresponding 1-O-acyl-β-D-glucopyranose tetraacetates. β-Anomers of g

2-(Trimethylsilyl)ethyl Glycosides. Synthesis, Anomeric Deblocking, and Transformation into 1,2-Trans 1-O-Acyl Sugars

Twenty-seven mono --> tetrasaccharidic 2-(trimethylsilyl)ethyl (TMSET) glycosides were synthesized by the Koenigs-Knorr-type method in combination with a wide range of standard reagents for glycoside synthesis and protecting-group chemistry.Variously protected TMSET glycosides were treated with BF3*Et2O (0.7-0.8 equiv) and different carboxylic anhydrides (1.1-15 equiv) in toluene at 22-55 deg C, which gave in one step the corresponding protected 1-O-acyl sugars.In the majority of cases, the yields of purified compounds exceeded 90percent and the anomeric configuration of the starting TMSET glyoside was conserved to a large extent (>95percent) in most of the 1-O-acylated products.Unprotected and acetyl-, benzoyl-, benzyl-, dimethyl-tert-butylsilyl-, and phthaloyl-protected mono-->tetrasaccharidic TMSET glycosides were anomerically deblocked by using trifluoroacetic acid in dichloromethane at 0-22 deg C for 10-30 min.The hemiacetal products were isolated in 88-96percent yield; all reagents and byproducts were volatile and easily removed.

POLYMER SUPPORTED SYNTHESIS OF 2,3,4,6-TETRA-O-ACETYL-β-D-GLUCOPYRANOSYL ESTERS OF AROMATIC CARBOXYLIC ACIDS

Aromatic carboxylic acids bound to Amberlyst A-26 react with α-acetobromoglucose to form 2,3,4,6-tetra-O-acetyl-1-O-aroyl-β-D-glucopyranose derivatives in good yield.Glucosylation occurs satisfactory with carboxylic acids and nitrophenols (pKa 7-4), but not with phenols whose pKa values higher (pKa ca 10).Selective glucosylation at the carboxylic group is easily achieved in the case of phenolic acids.