Cas no 4148-58-7 (Methyl 4,6-O-Benzylidene-a-D-mannopyranoside)

Methyl 4,6-O-Benzylidene-α-D-mannopyranoside is a protected derivative of D-mannose, widely used in carbohydrate chemistry and glycosylation research. The benzylidene group at the 4,6-positions provides selective protection, enhancing stability during synthetic manipulations while leaving the 2,3-hydroxyl groups available for further functionalization. This compound is particularly valuable in the synthesis of complex oligosaccharides and glycoconjugates due to its stereochemical control and compatibility with various reaction conditions. Its crystalline nature ensures high purity, facilitating precise characterization and reproducibility in experimental workflows. The compound’s robust protective group strategy makes it a preferred intermediate in medicinal chemistry and glycobiology studies.
Methyl 4,6-O-Benzylidene-a-D-mannopyranoside structure
4148-58-7 structure
Product Name:Methyl 4,6-O-Benzylidene-a-D-mannopyranoside
CAS No:4148-58-7
MF:C14H18O6
MW:282.289124965668
CID:331368
PubChem ID:11065894
Update Time:2025-10-29

Methyl 4,6-O-Benzylidene-a-D-mannopyranoside Chemical and Physical Properties

Names and Identifiers

    • a-D-Mannopyranoside, methyl4,6-O-(phenylmethylene)-
    • Methyl 4,6-O-Benzylidene-α-D-mannopyranoside
    • (4aR,6S,7S,8R,8aS)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
    • Methyl 4,6-O-Benzyli
    • METHYL 4,6-O-BENZYLIDENE-A-D-MANNOPYRANOSIDE
    • Methyl 4,6-O-benzylidene-alpha-D-mannopyranoside
    • α-D-Mannopyranoside, methyl 4,6-O-(phenylmethylene)-
    • Methyl 4,6-O-BenzylideneMannopyranoside
    • (4AR,6S,7S,8R,8aS)-6-methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
    • VVSWDMJYIDBTMV-ZWVDJKGDSA-N
    • Methyl-4,6-O-benzyliden-alpha-D-mannopyranoside
    • AKOS027326973
    • (2R,4AR,6S,7S,8R,8aS)-6-methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
    • Methyl 4,6-O-Benzylidene-
    • MFCD00211087
    • W-202708
    • CS-0452264
    • METHYL4,6-O-BENZYLIDENE-A-D-MANNOPYRANOSIDE
    • 65530-26-9
    • SCHEMBL6438852
    • CYTIDINE5-DIPHOSPHOCHOLINE
    • 4148-58-7
    • A-D-mannopyranoside
    • Methyl 4,6-O-(Phenylmethylene)-?-D-mannopyranoside; Methyl 4,6-O-Benzylidenemannopyranoside; NSC 170162;
    • Methyl 4,6-O-Benzylidene-a-D-mannopyranoside
    • Inchi: 1S/C14H18O6/c1-17-14-11(16)10(15)12-9(19-14)7-18-13(20-12)8-5-3-2-4-6-8/h2-6,9-16H,7H2,1H3/t9-,10-,11+,12-,13?,14+/m1/s1
    • InChI Key: VVSWDMJYIDBTMV-ZWVDJKGDSA-N
    • SMILES: O1[C@@H]([C@H]([C@H]([C@H]2[C@H]1COC(C1C=CC=CC=1)O2)O)O)OC

Computed Properties

  • Exact Mass: 282.11000
  • Monoisotopic Mass: 282.11
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 20
  • Rotatable Bond Count: 2
  • Complexity: 319
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 5
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 77.4A^2
  • XLogP3: -0.1

Experimental Properties

  • Melting Point: 141-143°C
  • PSA: 77.38000
  • LogP: 0.19370

Methyl 4,6-O-Benzylidene-a-D-mannopyranoside Customs Data

  • HS CODE:2932999099
  • Customs Data:

    China Customs Code:

    2932999099

    Overview:

    2932999099. Other heterocyclic compounds containing only oxygen heteroatoms. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Methyl 4,6-O-Benzylidene-a-D-mannopyranoside Suppliers

Suzhou Senfeida Chemical Co., Ltd
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(CAS:4148-58-7)METHYL 4,6-O-BENZYLIDENE-A-D-MANNOPYRANOSIDE
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Stock Status:in Stock
Quantity:200kg
Purity:99.9%
Pricing Information Last Updated:Friday, 19 July 2024 14:39
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Additional information on Methyl 4,6-O-Benzylidene-a-D-mannopyranoside

Methyl 4,6-O-Benzylidene-a-D-Mannopyranoside: A Comprehensive Overview

Methyl 4,6-O-Benzylidene-a-D-Mannopyranoside (CAS No. 4148-58-7) is a specialized carbohydrate derivative with significant applications in various fields, including pharmaceuticals, food additives, and cosmetics. This compound is derived from a-D-mannopyranoside, a naturally occurring sugar derivative, and undergoes a specific chemical modification to form the benzylidene derivative. The structure of Methyl 4,6-O-Benzylidene-a-D-Mannopyranoside is characterized by the presence of a benzylidene group at the 4 and 6 positions of the mannopyranoside ring, which imparts unique chemical and physical properties to the molecule.

The synthesis of Methyl 4,6-O-Benzylidene-a-D-Mannopyranoside involves a multi-step process that typically includes protection of the hydroxyl groups on the mannose ring followed by selective alkylation or acylation. The benzylidene group is introduced through a condensation reaction with benzaldehyde in the presence of an acid catalyst. This reaction not only stabilizes the ring structure but also enhances the compound's solubility and bioavailability. Recent studies have shown that this compound exhibits excellent stability under various pH conditions, making it suitable for use in aqueous environments.

One of the most promising applications of Methyl 4,6-O-Benzylidene-a-D-Mannopyranoside is in the field of drug delivery systems. Researchers have demonstrated that this compound can serve as an effective carrier for hydrophobic drugs due to its amphiphilic nature. The benzylidene group provides hydrophobicity, while the sugar moiety ensures biocompatibility and controlled drug release. In a recent study published in Journal of Controlled Release, scientists reported that this compound could encapsulate anti-cancer drugs with high efficiency and deliver them to target cells with minimal systemic toxicity.

In addition to its pharmaceutical applications, Methyl 4,6-O-Benzylidene-a-D-Mannopyranoside has gained attention in the food industry as a potential stabilizer and emulsifier. Its ability to form stable emulsions under high shear stress has been validated in several experiments conducted by food scientists at leading universities. A study published in Food Hydrocolloids highlighted its superior performance compared to traditional emulsifiers like lecithin and gum arabic.

The cosmetic industry has also explored the use of Methyl 4,6-O-Benzylidene-a-D-Mannopyranoside as a humectant and skin conditioning agent. Its unique molecular structure allows it to retain moisture effectively while providing a smooth texture to skincare products. Recent clinical trials have shown that formulations containing this compound exhibit enhanced skin penetration and improved efficacy compared to conventional moisturizers.

From an environmental perspective, Methyl 4,6-O-Benzylidene-a-D-Mannopyranoside has been evaluated for its biodegradability and eco-friendliness. Studies conducted under simulated environmental conditions indicate that this compound degrades efficiently under aerobic conditions without releasing harmful byproducts. This makes it an attractive alternative to synthetic polymers that are often associated with environmental pollution.

In conclusion, Methyl 4,6-O-Benzylidene-a-D-Mannopyranoside (CAS No. 4148-58-7) is a versatile compound with diverse applications across multiple industries. Its unique chemical structure and favorable properties make it an ideal candidate for advanced drug delivery systems, food additives, and cosmetic formulations. As research continues to uncover new potential uses for this compound, it is expected to play an increasingly important role in both scientific and industrial settings.

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Suzhou Senfeida Chemical Co., Ltd
(CAS:4148-58-7)METHYL 4,6-O-BENZYLIDENE-A-D-MANNOPYRANOSIDE
sfd21285
Purity:99.9%
Quantity:200kg
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