Cas no 183953-29-9 (Benzyl 2,3-Di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside)

Benzyl 2,3-Di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside is a protected glycoside derivative widely used in carbohydrate chemistry and glycosylation reactions. Its key advantages include enhanced stability due to multiple benzyl and benzylidene protecting groups, which selectively shield hydroxyl functionalities while allowing controlled deprotection for further synthetic modifications. The β-D-glucopyranoside configuration ensures stereochemical consistency in oligosaccharide synthesis. This compound serves as a versatile intermediate in the preparation of complex glycoconjugates, glycodendrimers, and other bioactive molecules. Its robust protective group strategy minimizes side reactions, improving yield and purity in multi-step synthetic routes. Suitable for research in glycoscience, it facilitates precise structural manipulation for drug discovery and biochemical studies.
Benzyl 2,3-Di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside structure
183953-29-9 structure
Product Name:Benzyl 2,3-Di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside
CAS No:183953-29-9
MF:C34H34O6
MW:538.630170345306
CID:4670097
PubChem ID:354333022
Update Time:2025-11-02

Benzyl 2,3-Di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside Chemical and Physical Properties

Names and Identifiers

    • 183953-29-9
    • (6S,7R,8As)-2-phenyl-6,7,8-tris(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
    • Benzyl 2,3-Di-O-benzyl-4,6-O-benzylidene-beta-D-glucopyranoside
    • Benzyl 2,3-Di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside
    • Inchi： 1S/C34H34O6/c1-5-13-25(14-6-1)21-35-31-30-29(24-38-33(40-30)28-19-11-4-12-20-28)39-34(37-23-27-17-9-3-10-18-27)32(31)36-22-26-15-7-2-8-16-26/h1-20,29-34H,21-24H2/t29?,30-,31?,32+,33?,34-/m0/s1
    • InChI Key： GQMVOFUMWKGWCK-FRCWTYOGSA-N
    • SMILES： O1[C@@H]([C@@H](C([C@@H]2C1COC(C1C=CC=CC=1)O2)OCC1C=CC=CC=1)OCC1C=CC=CC=1)OCC1C=CC=CC=1

Computed Properties

  • Exact Mass: 538.23553880g/mol
  • Monoisotopic Mass: 538.23553880g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 40
  • Rotatable Bond Count: 10
  • Complexity: 709
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 3
  • Undefined Atom Stereocenter Count : 3
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 5.4
  • Topological Polar Surface Area: 55.4?2

Experimental Properties

  • Melting Point: 136°C(lit.)

Benzyl 2,3-Di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside Security Information

  • Regulatory Condition Code：Class Q (sugars, alkaloids, antibiotics, hormones)

Benzyl 2,3-Di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
SHANG HAI MAI KE LIN SHENG HUA Technology Co., Ltd.
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Benzyl 2,3-Di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside
 183953-29-9 AR
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 ￥744.00 2022-09-29
SHANG HAI HAO HONG Biomedical Technology Co., Ltd.
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(4AR,6R,7R,8S,8aR)-6,7,8-tris(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine
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Benzyl 2,3-Di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside Related Literature

Additional information on Benzyl 2,3-Di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

Benzyl 2,3-Di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (CAS No. 183953-29-9): A Comprehensive Overview

Benzyl 2,3-Di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (CAS No. 183953-29-9) is a highly specialized carbohydrate derivative widely used in organic synthesis and pharmaceutical research. This compound belongs to the class of benzylated glycosides, which are pivotal intermediates in the synthesis of complex oligosaccharides and glycoconjugates. Its unique structure, featuring multiple benzyl protecting groups, makes it an invaluable tool for chemists working on glycosylation reactions and carbohydrate chemistry.

The molecular structure of Benzyl 2,3-Di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside includes a β-D-glucopyranoside core, which is protected at the 2,3-positions by benzyl groups and at the 4,6-positions by a benzylidene acetal. This configuration ensures selective reactivity, allowing researchers to perform targeted modifications. The compound's stability under various reaction conditions has made it a favorite in medicinal chemistry and drug development, particularly for designing glycosidase inhibitors and antiviral agents.

In recent years, the demand for benzylated sugar derivatives like Benzyl 2,3-Di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside has surged due to their role in developing glycoscience-based therapeutics. Researchers are particularly interested in its applications for COVID-19 drug discovery, as glycosylation plays a critical role in viral entry mechanisms. Additionally, the compound's utility in cancer immunotherapy and vaccine adjuvants has sparked significant interest in the biopharmaceutical industry.

The synthesis of Benzyl 2,3-Di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside typically involves multi-step organic transformations, including protecting group strategies and stereoselective glycosylation. Advanced techniques like microwave-assisted synthesis and flow chemistry have been explored to improve yield and scalability. These innovations align with the growing trend toward green chemistry and sustainable synthesis, addressing environmental concerns in chemical manufacturing.

From a commercial perspective, Benzyl 2,3-Di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside is available through specialized chemical suppliers and custom synthesis providers. Its pricing reflects the complexity of its production, with purity levels ranging from >95% to >98% for research-grade material. The compound is often shipped under controlled conditions to ensure stability, as moisture and temperature can affect its performance in sensitive reactions.

Looking ahead, the future of Benzyl 2,3-Di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside appears promising, with ongoing studies exploring its potential in glycan microarray technology and biomarker discovery. As the field of glycobiology continues to expand, this compound will likely remain a cornerstone for innovative research in both academia and industry.

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