14125-75-8

Usage

Uses

Used in Organic Synthesis:
(-)-TETRA-O-BENZOYL-2-HYDROXY-D-GLUCAL is used as a chiral building block for the synthesis of natural products, contributing to the development of complex organic molecules with desired stereochemistry.
Used in Asymmetric Synthesis:
In the field of asymmetric synthesis, (-)-TETRA-O-BENZOYL-2-HYDROXY-D-GLUCAL is utilized as a chiral auxiliary to control the stereochemistry of reactions, ensuring the production of enantiomerically pure compounds.
Used in Pharmaceutical Industry:
(-)-TETRA-O-BENZOYL-2-HYDROXY-D-GLUCAL is used as a key intermediate in the synthesis of pharmaceutical compounds, enabling the production of drugs with specific stereochemical requirements for enhanced efficacy and selectivity.
Used in Chemical Research:
In the realm of chemical research, (-)-TETRA-O-BENZOYL-2-HYDROXY-D-GLUCAL is employed as a versatile compound for studying reaction mechanisms, exploring new synthetic routes, and developing innovative methodologies in organic chemistry.

Upstream product

• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 109-89-7 diethylamine 
• 31273-58-2 1-(7-hydroxy-2,2-dimethylchroman-6-yl)ethanone 
• 140-10-3 (E)-3-phenylacrylic acid 
• 1615-02-7 3-(4-chlorophenyl)prop-2-enoic acid 
• 555-68-0 (E)-3-Nitrocinnamic acid 
• 14737-89-4 3,4-dimethoxy-trans-cinnamic acid 
• 1552-96-1 p-dimethylaminocinnamic acid 
• 118-93-4 o-hydroxyacetophenone 
• 90-02-8 salicylaldehyde 
• 118-61-6 2-hydroxy-benzoic acid ethyl ester 
• 71591-75-8 sodium 2-mercaptothiazolinate 
• 14262-85-2 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl iodide 
• 1221151-98-9 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate 

Downstream Products

• 127844-94-4 C₃₈H₃₀BrNO₁₁ 
• 53942-33-9 (+)-(5S,6R)-3,5-Bis(benzoyloxy)-6-(benzoyloxymethyl)-5,6-dihydro-2H-pyran-2-one 
• 122359-43-7 C₃₄H₂₅ClO₁₀ 
• 42889-91-8 (5'-formylfuran-2'-yl)methyl benzoate 
• 119870-15-4 Benzoic acid (2S,6S)-6-isopropoxy-5-oxo-5,6-dihydro-2H-pyran-2-ylmethyl ester 
• 114682-31-4 2-propyl 2,4,6-tri-O-benzoyl-3-deoxy-α-D-erythro-hex-2-enopyranoside 
• 52080-35-0 Tetra-O-benzoyl-α-D-arabino-[2]hexosul-1,5-ose 
• 65725-69-1 2,3,4,6-tetra-O-benzoyl-2-bromo-α-D-glucopyranosyl bromide 
• 52080-38-3 (2R,6S)-2,4-dibenzoyloxy-6-benzoyloxymethyl-2H-pyran-3(6H)-one 
• 75414-21-0 3,4,6-tri-O-benzoyl-1,5-anhydro-D-fructose E-oxime 
• 75414-41-4 (6S)-4-benzoyloxy-6-benzoyloxymethyl-2H-pyran-3(6H)-one 
• 111718-45-7 C₂₅H₂₂O₆ 
• 111718-45-7 C₂₅H₂₂O₆ 
• 111718-43-5 C₂₄H₂₄O₆ 

Relevant academic research and scientific papers

Mechanistic insights into the gold(I)-Catalyzed activation of glycosyl Ortho -Alkynylbenzoates for Glycosidation

Anomerization, which involves cleavage and formation of the anomeric C-O bond, is of fundamental importance in the carbohydrate chemistry. Herein, the unexpected gold(I)-catalyzed anomerization of glycosyl ortho-alkynylbenzoates has been studied in detail. Especially, crossover experiments in the presence of an exogenous isochromen-4-yl gold(I) complex confirm that the anomerization proceeds via the exocleavage mechanism, involving (surprisingly) the addition of the isochromen-4-yl gold(I) complex onto a sugar oxocarbenium (or dioxolenium) and an elimination of LAu+ from the vinyl gold(I) complex. The inhibitory effect of the exogenous isochromen-4-yl gold(I) complex when in stoichiometric amount on the anomerization has guided us to disclose an isochromen-4-yl gem-gold(I) complex, which is inactive in catalysis but in equilibrium with the monogold(I) complex and the LAu+ catalyst. The proposed key intermediate in the anomerization, a transient glycosyloxypyrylium species, is successfully trapped via a cycloaddition reaction with n-butyl vinyl ether as a dienophile. SN2-like substitution of the initially formed glycosyloxypyrylium intermediate has then been achieved to a large extent via charging with acceptors in an excess amount to lead to the corresponding glycosides in a stereoselective manner.

1,2-Trans-selective synthesis of glycosyl boranophosphates and their utility as building blocks for the synthesis of phosphodiester-linked disaccharides

Figure Presented A highly 1,2-trans-selective synthesis of glycosyl boranophosphate derivatives by glycosylation of dimethyl boranophosphate with glycosyl iodides was developed. A study on the reaction mechanism indicated that the stereoselectivity of the

A method for the syntheses of Enopyranosides

Sodium hydride (NaH) in hexamethylphosphoric triamide (HMPA) has been introduced as an economical and efficient reagent towards the creation of 1, 2- or 5, 6-enopyranosides from the corresponding halogenated or tosylated pyranosides. NaH/HMPA has several advantages compared to NaH/DMF: elimination products are produced in high yields even from sterically-hindered halides as well as tosylates. 2009 Bentham Science Publishers Ltd.

Expedient conversion of d-glucose into 1,5-anhydro-d-fructose and into single stereogenic-center dihydropyranones, suitable six-carbon scaffolds for concise syntheses of the soft-coral constituents (-)-bissetone and (-)-palythazine

High-yielding protocols are described to convert d-glucose-via hydroxylaminolysis of its hydroxyglucal esters, followed by deoximination and β-elimination of acid-into dihydropyranone building blocks with a single stereogenic center. Their versatility as enantiopure six-carbon scaffolds is highlighted by excellent regio- and stereocontrol in a variety of addition reactions and by their straightforward use as building blocks for the concise syntheses of the soft-coral constituents bissetone and palythazine in enantiopure form, thereby proving their absolute configuration. Moreover, several procedures are detailed to convert hydroxyglucal esters into 1,5-anhydro-d-fructose, their parent sugar, the direct low-temperature de-O-acylation being the most suitable for preparative purposes, as long as its access via enzymatic degradation of starch is not implemented on an appreciable scale.

S-thiazolinyl (STaz) glycosides as versatile building blocks for convergent selective, chemoselective, and orthogonal oligosaccharide synthesis

In the aim of developing new procedures for efficient oligosaccharide assembly, a range of 5-thiazolinyl (STaz) glycosides have been synthesized. These novel derivatives were evaluated against a variety of reaction conditions and were shown to be capable of being chemoselectively activated in the armed-disarmed fashion. More over, the S-thiazolinyl moiety exhibited a remarkable propensity for selective activation over other common leaving groups. Conversely, a variety of leaving groups could be selectively activated over the STaz moiety, which, in turn, allowed STaz/S-ethyl and STaz/S-phenyl orthogonal approaches. To demonstrate versatility of novel STaz derivatives, a number of oligosaccharide targets have been synthesized in a convergent selective, orthogonal, and chemoselective fashion.

Potent, versatile, and stable: Thiazolyl thioglycosides as glycosyl donors

Donating with a difference: Thiazolyl (Taz) substituted thioglycosides have been successfully used in the synthesis of both 1,2-trans- and 1,2-cis-glycosides and also have found application in convergent oligosaccharide synthesis. In addition, this study

Sodium hydride/hexamethylphosphoric triamide: A new and efficient reagent towards the synthesis of protected 1,2- and 5,6-enopyranosides

A new method for the elimination of hydrogen halides and p-toluenesulfonic acid from sugar moieties using sodium hydride (NaH) in hexamethylphosphoric triamide (HMPA) at room temperature is reported. NaH/HMPA has several advantages compared to NaH/DMF: elimination products are produced in high yields even from sterically hindered starting materials, and not only from halides, but also tosylates.

A CONVENIENT PREPARATION OF HEX-5,6-ENOPYRANOSIDES

Hex-5,6-enopyranosides were conveniently prepared from 6-halohexopyranosides by treatment with sodium hydride in dimethylformamide.Simultaneous benzylation of free hydroxyl groups can be achieved.

THE REACTION OF 2-HYDROXYGLYCAL ESTERS WITH ALCOHOLS IN THE PRESENCE OF N-IODOSUCCINIMIDE, STEREOSELECTIVE SYNTHESIS OF α ANOMERS OF ALKYL-3-DEOXYHEX-2-ENOPYRANOSIDES AND 3,4-DIDEOXYHEX-3-ENOPYRANOSID-2-ULOSES

Reaction of 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabino-hex-1-enitol (1; 2-hydroxyglucal tetraacetate) with 1.0-1.5 mol of primary, secondary, or tertiary alcohols, in the presence of 0.1-1.0 mol of N-iodosuccinimide (NIS) in acetonitrile as solvent, aff