74801-29-9

Usage

Uses

Used in Organic Synthesis:
Phenyl2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside is used as a key intermediate in the synthesis of complex organic molecules. Its unique structure allows for the formation of various functional groups and the construction of diverse molecular architectures. Phenyl2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside is particularly useful in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Phenyl2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside is used as a building block for the development of new drugs. Its versatility and reactivity enable the synthesis of a wide range of bioactive compounds with potential therapeutic applications. Phenyl2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside can be used to create novel drug candidates for the treatment of various diseases and disorders.
Used in Agrochemical Industry:
Phenyl2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside is also used in the agrochemical industry for the synthesis of new pesticides and other crop protection agents. Its unique structure allows for the development of innovative molecules with improved efficacy, selectivity, and environmental compatibility.
Used in Specialty Chemicals:
In the specialty chemicals sector, Phenyl2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside is employed in the synthesis of various high-value compounds, such as fragrances, dyes, and functional materials. Its unique properties make it an ideal starting material for the development of novel specialty chemicals with specific applications and performance characteristics.

InChI:InChI=1/C40H40O5S/c1-6-16-31(17-7-1)26-41-30-36-37(42-27-32-18-8-2-9-19-32)38(43-28-33-20-10-3-11-21-33)39(44-29-34-22-12-4-13-23-34)40(45-36)46-35-24-14-5-15-25-35/h1-25,36-40H,26-30H2/t36?,37-,38?,39?,40-/m0/s1

Upstream product

• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 14365-16-3 bis-(phenylthio)-dibutylstannane 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 108-98-5 thiophenol 
• 78890-59-2 Methoxy-acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 144-55-8 sodium hydrogencarbonate 
• 882-33-7 diphenyldisulfane 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 100-39-0 benzyl bromide 
• 13992-16-0 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 365534-59-4 2'-(benzyloxycarbonyl)benzyl α-D-mannopyranoside 
• 220662-68-0 2-{[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)oxy]methyl}benzoic acid 
• 2936-70-1 (2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 

Downstream Products

• 25320-59-6 tetra-O-benzyl glucopyranosyl chloride 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 165680-85-3 methyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 130050-83-8 methyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside 
• 77117-44-3 methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 64694-18-4 methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside 
• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 1595290-37-1 C₃₇H₃₈O₆ 
• 1595290-39-3 C₃₇H₃₈O₆ 
• 1595290-41-7 C₃₈H₄₀O₅ 
• 776313-98-5 5,6,7,9-tetra-O-benzyl-1,2,3-trideoxy-D-gluco-non-1-eno-4-ulopyranose 
• 55094-26-3 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-α-D-glucopyranoside 
• 64694-18-4 methyl 4-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)(1→4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 78153-79-4 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl fluoride 

Relevant academic research and scientific papers

First synthesis of bacillus cereus Ch HF-PS cell wall trisaccharide repeating unit

The first total synthesis of Ch HF-PS, a cell wall trisaccharide repeating unit of B. cereus, is reported. The synthetic trisaccharide is appended with an aminopropyl linker at the reducing end to allow for conjugation to proteins and microarrays. The con

Electrochemical Synthesis of Glycosyl Fluorides Using Sulfur(VI) Hexafluoride as the Fluorinating Agent

This manuscript describes the electrochemical synthesis of 17 different glycosyl fluorides in 73-98% yields on up to a 5 g scale that relies on the use of SF6 as an inexpensive and safe fluorinating agent. Cyclic voltammetry and related mechanistic studies carried out subsequently suggest that the active fluorinating species generated through the cathodic reduction of SF6 are transient under these reductive conditions and that the sulfur and fluoride byproducts are effectively scavenged by Zn(II) to generate benign salts.

Visible Light Enables Aerobic Iodine Catalyzed Glycosylation

A versatile protocol for light induced catalytic activation of thioglycosides using iodine as an inexpensive and readily available photocatalyst was developed. Oxygen serves as a green and cost-efficient terminal oxidant and irradiation is performed with a common household LED-bulb. The scope of this glycosylation protocol was investigated in the synthesis of O-glycosides with yields up to 95 %.

Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones to Prepare C-Aryl Glycals and Acyclic Vinyl Ethers

We demonstrate that readily available and bench-stable α-oxo-vinylsulfones are competent electrophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling reactions. The C-sulfone bond in the α-oxo-vinylsulfone motif is cleaved chemoselectively in these reactions, furnishing C-aryl glycals or acyclic vinyl ethers in high yields. These reactions proceed under mild conditions and tolerate a remarkable scope of heterocycles and functional groups. Preliminary mechanistic studies revealed the importance of an α-heteroatom in facilitating these transformations.

Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones to Prepare C-Aryl Glycals and Acyclic Vinyl Ethers

We demonstrate that readily available and bench-stable α-oxo-vinylsulfones are competent electrophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling reactions. The C-sulfone bond in the α-oxo-vinylsulfone motif is cleaved chemoselectively in these reactions, furnishing C-aryl glycals or acyclic vinyl ethers in high yields. These reactions proceed under mild conditions and tolerate a remarkable scope of heterocycles and functional groups. Preliminary mechanistic studies revealed the importance of an α-heteroatom in facilitating these transformations.

Dissection of the effects that govern thioglucoside and thiomannoside reactivity

Neighboring group effects were investigated in gluco- and manno-configured thioglycosides under NIS/TfOH activation. Donors possessing a 2-O-benzoyl group that are capable (1,2-trans) and incapable (1,2-cis) of exerting nucleophilic push were compared wit

Remote Electronic Effects by Ether Protecting Groups Fine-Tune Glycosyl Donor Reactivity

It was established that para-substituted benzyl ether protecting groups affect the reactivity of glycosyl donors of the thioglycoside type with the N-iodosuccinimide/triflic acid promoter system. Having electron donating p-methoxybenzyl ether (PMB) groups increased the reactivity of the donor in comparison to having electron withdrawing p-chloro (PClB) or p-cyanobenzyl ether (PCNB) protecting groups, which decreased the reactivity of the glycosyl donor relative to the parent benzyl ether (Bn) protected glycosyl donor. These findings were used to perform the first armed-disarmed coupling between two benzylated glucosyl donors by tuning their reactivity. In addition, the present work describes a highly efficient palladium catalyzed multiple cyanation and methoxylation of p-chlorobenzyl protected thioglycosides. The results of this paper regarding both the different electron withdrawing properties of various benzyl ethers and the efficient and multiple protecting group transformations are applicable in general organic chemistry and not restricted to carbohydrate chemistry.

Facile Diastereoseparation of Glycosyl Sulfoxides by Chiral Stationary Phase

Separation of the diastereomers of glycosyl sulfoxides differing in the sulfur chirality has been difficult. This article presents a fast and scalable method for their diastereoseparation using a chiral stationary phase. The usefulness of this method was

Directing effect by remote electron-withdrawing protecting groups at O-3 or O-4 position of donors in glucosylations and galactosylations

Glucosylations and galactosylations of various acceptors with donors possessing an electron-withdrawing benzylsulfonyl, benzoyl, or acetyl group at the O-3 or O-4 position were performed. A β-directing effect by the benzylsulfonyl group at O-3 of the glucosyl donors and by the benzylsulfonyl and acyl groups at O-4 of the glucosyl donors was observed. In contrast, acyl groups at O-3 of the glucosyl donors and acyl groups at O-3 and O-4 of the galactosyl donors exhibited an α-directing effect. The α-directing effect is partly considered to remote participation of the acyl groups, whereas the β-directing effect is somewhat attributed to the SN2-like reaction of the acceptor with the glycosyl triflate or the contact ion pair, which is stabilized by remote electron-withdrawing groups. Further evidence for the stability of the α-glycosyl triflates was determined by a low-temperature NMR study.

NKT CELL LIGANDS AND METHODS OF USE

Alpha-glycosylceramide compounds capable of activating NKT cells and compositions thereof are disclosed. Methods for activating NKT cells, methods of stimulating an immune response in a subject, and methods of treating cancer, infectious diseases, autoimmune diseases and disorders, or allergy diseases or disorders with the compounds and compositions are also disclosed.