64978-35-4

Basic information

• Product Name: D-arabino-Hex-1-enitol, 1,5-anhydro-2-deoxy-3,4,6-tris-O-(phenylmethyl)-1-C-(phenylsulfonyl)-
• Synonyms: D-arabino-Hex-1-enitol, 1,5-anhydro-2-deoxy-3,4,6-tris-O-(phenylmethyl)-1-C-(phenylsulfonyl)-
• CAS NO: 64978-35-4
• Molecular Formula: C₃₃H₃₂O₆S
• Molecular Weight: 556.67
• Mol File: 64978-35-4.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: D-arabino-Hex-1-enitol, 1,5-anhydro-2-deoxy-3,4,6-tris-O-(phenylmethyl)-1-C-(phenylsulfonyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: D-arabino-Hex-1-enitol, 1,5-anhydro-2-deoxy-3,4,6-tris-O-(phenylmethyl)-1-C-(phenylsulfonyl)-(64978-35-4)
• EPA Substance Registry System: D-arabino-Hex-1-enitol, 1,5-anhydro-2-deoxy-3,4,6-tris-O-(phenylmethyl)-1-C-(phenylsulfonyl)-(64978-35-4)

Safety Data

• Hazardous Substances Data: 64978-35-4(Hazardous Substances Data)

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

• 110390-65-3 1-((4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-5,6-dihydro-4H-pyran-2-yl)-cyclohex-2-enol 
• 131771-59-0 4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enono-1,5-lactone 
• 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 articles and documents

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.

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-