Cas no 129081-01-2 (Phenyl 2,3-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside)

Phenyl 2,3-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside is a protected thioglycoside derivative widely used in carbohydrate chemistry and glycosylation reactions. Its key advantages include enhanced stability due to the benzyl-protected hydroxyl groups at the 2- and 3-positions, which prevent unwanted side reactions during synthetic processes. The thioglycoside moiety serves as a versatile glycosyl donor, enabling efficient glycosidic bond formation under mild conditions. This compound is particularly valuable in oligosaccharide synthesis, offering selective reactivity and compatibility with various protecting group strategies. Its well-defined stereochemistry ensures high regioselectivity, making it a reliable intermediate for complex carbohydrate-based research and pharmaceutical applications.
Phenyl 2,3-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside structure
129081-01-2 structure
Product Name:Phenyl 2,3-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside
CAS No:129081-01-2
MF:C26H28O5S
MW:452.562526702881
CID:2857858
Update Time:2025-06-30

Phenyl 2,3-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside Chemical and Physical Properties

Names and Identifiers

    • Phenyl 2,3-Di-O-benzyl-1-thio-β-D-glucopyranoside
    • Phenyl 2,3-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside
    • β-D-Glucopyranoside, phenyl 2,3-bis-O-(phenylmethyl)-1-thio-
    • Phenyl 2,3-di-O-benzyl-b-D-thioglucopyranoside
    • Phenyl2,3-Di-O-benzyl-1-thio-β-D-glucopyranoside
    • Inchi： 1S/C26H28O5S/c27-16-22-23(28)24(29-17-19-10-4-1-5-11-19)25(30-18-20-12-6-2-7-13-20)26(31-22)32-21-14-8-3-9-15-21/h1-15,22-28H,16-18H2/t22-,23-,24+,25-,26+/m1/s1
    • InChI Key： RCNHWIGTXCJGFF-RTJMFUJLSA-N
    • SMILES： S(C1=CC=CC=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](OCC2=CC=CC=C2)[C@H]1OCC1=CC=CC=C1

Experimental Properties

  • Density: 1.28±0.1 g/cm3 (20 oC 760 Torr),
  • Melting Point: 111-112 oC
  • Solubility: Insuluble (9.1E-3 g/L) (25 oC),
  • PSA: 93.45000
  • LogP: 4.02760

Phenyl 2,3-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
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MP04352-1 g
Phenyl 2,3-di-O-benzyl-b-D-thioglucopyranoside
 129081-01-2
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 $2,310.00 2023-01-03

Phenyl 2,3-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside Related Literature

Additional information on Phenyl 2,3-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside

Comprehensive Overview of Phenyl 2,3-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside (CAS No. 129081-01-2)

Phenyl 2,3-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside (CAS No. 129081-01-2) is a specialized glycoside derivative with significant applications in organic synthesis and pharmaceutical research. This compound, characterized by its thioglycoside structure, serves as a key intermediate in the preparation of complex carbohydrates and glycoconjugates. Its unique benzyl-protected hydroxyl groups and phenylthio aglycone make it a versatile building block for stereoselective glycosylation reactions, a topic of high interest in modern carbohydrate chemistry.

In recent years, the demand for synthetic glycosides like Phenyl 2,3-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside has surged due to their role in drug discovery and glycobiology. Researchers frequently search for "thioglycoside applications" or "CAS 129081-01-2 solubility," reflecting the compound's relevance in enzyme inhibition studies and glycosidase inhibitor design. Its stability under acidic conditions and compatibility with protecting group strategies further enhance its utility in multistep syntheses.

The compound's molecular structure features a beta-D-glucopyranoside core with phenylmethyl (benzyl) groups at the 2- and 3-positions, offering selective deprotection opportunities. This aligns with current trends in "green chemistry" inquiries, as scientists explore atom-efficient routes to modify such scaffolds. Discussions on platforms like ResearchGate often highlight its use in "click chemistry" and "carbohydrate-based vaccine development," underscoring its interdisciplinary importance.

From a spectroscopic perspective, 129081-01-2 exhibits distinct NMR peaks for aromatic protons (7.2–7.4 ppm) and anomeric carbons (~85 ppm in 13C NMR), critical for purity validation. Analytical queries such as "HPLC methods for thioglycosides" or "CAS 129081-01-2 MSDS" (though non-hazardous) indicate user focus on quality control protocols. The compound's crystalline form and melting point data are also frequently cited in patent literature.

Emerging applications include its role in glycosyl donor-acceptor systems, particularly in studies addressing "diabetes drug targets" and "antiviral glycotherapeutics." Its phenylthio moiety enables radical-mediated glycosylations, a technique gaining traction in bioconjugation workflows. Notably, the compound's lipophilicity (enhanced by benzyl groups) makes it valuable for membrane permeability studies, a hot topic in "oral drug delivery" research.

In summary, Phenyl 2,3-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside (CAS No. 129081-01-2) represents a highly functionalized scaffold bridging traditional glycoscience and cutting-edge therapeutics. Its structural features cater to both academic investigations and industrial-scale processes, answering contemporary search trends like "sustainable glycosylation methods" and "CAS 129081-01-2 suppliers." As glycomics advances, this compound's role in precision medicine and material science is poised to expand further.

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