64978-35-4

Upstream product

• 2936-70-1 phenyl 1-thio-D-glucopyranoside 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside 
• 83-87-4 D-glucose pentaacetate 
• 91602-61-8 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α/β-D-glucopyranoside 
• 108-98-5 thiophenol 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 64978-34-3 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranosyl sulfone 

Downstream Products

• 105938-06-5 ((4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-5,6-dihydro-4H-pyran-2-yl)-trimethyl-silane 
• 110390-66-4 methyl (4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-5,6-dihydro-4H-pyran-2-carboxylate 
• 110390-67-5 Bis-((4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-5,6-dihydro-4H-pyran-2-yl)-methanone 
• 110390-64-2 ((4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-5,6-dihydro-4H-pyran-2-yl)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol 
• 105938-02-1 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 91780-41-5 3,4,6-tri-O-benzyl-1,2-dideoxy-1,5-anhydro-D-arabino-hexitol 
• 130912-27-5 (2R,3S,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-phenyl-3,4-dihydro-2H-pyran 
• 130912-30-0 1-allyl-3,4,6-tri-O-benzyl-D-glucal 

Relevant academic research and scientific papers

Preparation method of diabetes-treating medicine, namely ipragliflozin or derivative thereof

The invention provides a preparation method of a diabetes-treating medicine, namely ipragliflozin or a derivative thereof. According to the preparation method, alpha-O-alkenyl sulfone is used as an electrophilic reagent for the Suzuki-Miyaura coupling reaction; the reaction raw material alpha-O-alkenyl sulfone is simple to prepare and stable in structure, and can overcome the defects of instability, preparation difficulty and the like when organic halide and sulfonic acid are used as electrophilic reagents for the Suzuki-Miyaura coupling reaction. Meanwhile, the reaction are mild in reaction conditions, compatible with a wide range of heterocyclic rings and various functional groups, high in yield and capable of realizing large-scale process production. Since alpha-O-alkenyl sulfone is used as the electrophilic reagent for the Suzuki-Miyaura coupling reaction, high-yield generation of aryl glucoside and open-chain alkenyl ether can be realized, medicines for treating type 2 diabetes mellitus, namely ipragliflozin and 2-deoxyipragliflozin can also be prepared, and the application scope of the preparation method is wide.

Suzuki-Miyaura coupling reaction using alpha-O-alkenyl sulfone as electrophilic reagent and application thereof

The invention provides a Suzuki-Miyaura coupling reaction using alpha-O-alkenyl sulfone as an electrophilic reagent. The reaction comprises the following steps: weighing alpha-O-alkenyl sulfone, an organic boron reagent, a ligand, an alkali and a catalyst, and carrying out reacting in a solvent. The invention also provides application of the coupling reaction. According to the invention, alpha-O-alkenyl sulfone is used as the electrophilic reagent for the Suzuki-Miyaura coupling reaction, and the reaction raw material alpha-O-alkenyl sulfone is simple to prepare and stable in structure, and can overcome the defects of instability, preparation difficulty and the like when organic halide and sulfonic acid are used as electrophilic reagents for the Suzuki-Miyaura coupling reaction. Meanwhile,the reaction are mild in reaction conditions, compatible with a wide range of heterocyclic rings and various functional groups, high in yield and capable of realizing large-scale process production.Since the alpha-O-alkenyl sulfone is used as the electrophilic reagent for the Suzuki-Miyaura coupling reaction, high-yield generation of aryl glucoside and open-chain alkenyl ether can be realized, medicines for treating type 2 diabetes mellitus, namely ipragliflozin and 2-deoxyipragliflozin can also be prepared, and the application scope of the reaction is wide.

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.

A single-process desulfonylation of perbenzylated-α- and -β-D-glycopyranosyl phenyl (tert-butyl)sulfones

Phenyl and/or tert-butyl α or β-D-glucopyranosyl sulfones were treated with lithium aluminum hydride and potassium hydroxide respectively to afford conveniently desulfonylated products (4 and 5). From the former reductive process was isolated the 2-deoxy-

Synthesis of C-glycopyranosyl compounds by a palladium-catalyzed coupling reaction of 1-tributylstannyl-D-glucals with organic halides

1-Tributylstannyl-D-glucals, prepared from the corresponding 1-phenylsulfonyl-D-glucals, were coupled efficiently to various organic halides in the presence of a palladium(0) catalyst.This mild reaction is specially useful for the preparation of 1-C-aryl-

A Convenient Synthesis of Pyranoid Ene Lactones from Phenyl Glycosyl Sulfones

O-Benzyl protected pyranoid ene lactones (5,6-dihydro-2H-pyran-2-ones) 4a-c, 8 were obtained in high yield in a two-step procedure.Treatment of the phenyl glycosyl sulfones 2a-d, 6, which were readily prepared from their corresponding sulfides, with lithi

PREPARATION AND USE OF LITHIATED GLYCALS: VINYLIC DEPROTONATION VERSUS TIN-LITHIUM EXCHANGE FROM 1-TRIBUTYLSTANNYL GLYCALS

Methods for preparing glycals lithiated at the C-1 atom by either direct vinylic deprotonation or by tin-lithium exchange from the corresponding 1-tri-n-butylstannyl glycals are described.Alkylation of these lithiated anions wih various electrophiles lead