14125-75-8

Basic information

• Product Name: (-)-TETRA-O-BENZOYL-2-HYDROXY-D-GLUCAL
• Synonyms: 1,5-ANHYDRO-3,4,6-TRI-O-BENZOYL-2-BENZOYLOXY-D-ARABINO-HEX-1-ENITOL;1-DEOXY-D-GLUCO-HEX-1-ENOPYRANOSE TETRABENZOATE;(-)-TETRA-O-BENZOYL-2-HYDROXY-D-GLUCAL;D-arabino-Hex-1-enitol, 1,5-anhydro-, tetrabenzoate;(-)-TETRA-O-BENZOYL-2-HYDROXY-D-GLUCAL 98+%;2,3,4,6-Tetra-O-benzoyl-1-deoxy-D-arabino-hex-1-enopyranose;(-)-TETRA-O-BENZOYL-2-HYDROXY-D-GLUCAL F
• CAS NO: 14125-75-8
• Molecular Formula: C₃₄H₂₆O₉
• Molecular Weight: 578.56
• Mol File: 14125-75-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: 122-124 °C(lit.)
• Appearance: /
• CAS DataBase Reference: (-)-TETRA-O-BENZOYL-2-HYDROXY-D-GLUCAL(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-TETRA-O-BENZOYL-2-HYDROXY-D-GLUCAL(14125-75-8)
• EPA Substance Registry System: (-)-TETRA-O-BENZOYL-2-HYDROXY-D-GLUCAL(14125-75-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 14125-75-8(Hazardous Substances Data)

Usage

General Description

(-)-Tetra-O-benzoyl-2-hydroxy-D-glucal is a chemical compound that is often used in organic synthesis. It is a sugar derivative with four benzoyl groups attached to the hydroxyl groups of the glucose molecule. (-)-TETRA-O-BENZOYL-2-HYDROXY-D-GLUCAL has been studied for its potential use in the preparation of chiral building blocks for the synthesis of natural products. It is also used as a chiral auxiliary in asymmetric synthesis, where it can help to control the stereochemistry of reactions. Overall, (-)-Tetra-O-benzoyl-2-hydroxy-D-glucal is a valuable tool in organic chemistry for creating complex molecules with specific stereochemical properties.

Upstream product

• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 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 
• 1221151-98-9 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate 
• 14262-85-2 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl iodide 
• 5554-48-3 Tetrahydro-1,3-thiazin-2-thion 
• 17374-18-4 [1,3]oxazinane-2-thione 

Downstream Products

• 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 
• 111718-43-5 C₂₄H₂₄O₆ 
• 111718-47-9 ((2S,5S)-5-hydroxy-5-(2-oxopropyl)-4-oxo-tetrahydro-2H-pyran-2-yl)methyl benzoate 
• 111718-49-1 ((2S,5R)-5-hydroxy-5-(2-oxopropyl)-4-oxo-tetrahydro-2H-pyran-2-yl)methyl benzoate 
• 111718-42-4 (2S,5S)-5-allyl-5-benzoyloxy-2-benzoyloxymethyltetrahydropyran-4-one 
• 111718-41-3 (2S,5S)-5-benzoyloxy-2-benzoyloxymethyl-5-methyltetrahydropyran-4-one 
• 111718-46-8 3,6-di-O-benzoyl-4-deoxy-4-C-methyl-1,5-anhydro-D-frucrose 
• 75414-32-3 1,5-anhydro-3,4,6-tri-O-benzoyl-D-fructose 
• 75414-38-9 (6S)-4-benzoyloxy-6-benzoyloxymethyl-2H-pyran-3(6H)-one 
• 52080-38-3 (2R,6S)-2,4-dibenzoyloxy-6-benzoyloxymethyl-2H-pyran-3(6H)-one 

Relevant articles and documents

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.

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.

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.