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1,3,4,6-TETRA-O-ACETYL-BETA-D-MANNOPYRANOSE is a chemical compound that serves as an intermediate in the synthesis of various biologically active molecules. It is a derivative of beta-D-mannopyranose, a monosaccharide, with four acetyl groups attached to its hydroxyl groups. This modification enhances its reactivity and stability, making it a valuable building block in organic synthesis.

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  • 18968-05-3 Structure
  • Basic information

    1. Product Name: 1,3,4,6-TETRA-O-ACETYL-BETA-D-MANNOPYRANOSE
    2. Synonyms: 1,3,4,6-Tetraacetate β-D-Mannopyranose;1,3,4,6-O-Tetraacetyl-β-D-Mannopyranose;[(2R,3R,4R,5S,6S)-3,4,6-triacetyloxy-5-hydroxyoxan-2-yl]methyl acetate;(2S,3S,4R,5R,6R)-6-(Acetoxymethyl)-3-hydroxytetrahydro-2H-pyran-2,4,5-triyl triacetate;1,3,4,6-Tetra-O-acetyl-β1,3,4,6-TETRA-O-ACETYL-BETA-D-MANNOPYRANOSE;1,2,3,4-TETRA-O-ACETYL-BETA-D-MANNOPYRANOSE;1,3,4,6-Tetra-O-acetyl-?D-mannopyranose
    3. CAS NO:18968-05-3
    4. Molecular Formula: C14H20O10
    5. Molecular Weight: 348.3
    6. EINECS: N/A
    7. Product Categories: Intermediates & Fine Chemicals;Labeling and Diagnostics Reagents;Pharmaceuticals;chiral;Biochemistry;O-Substituted Sugars;Sugars;Carbohydrates & Derivatives
    8. Mol File: 18968-05-3.mol
  • Chemical Properties

    1. Melting Point: 160-161 °C(lit.)
    2. Boiling Point: 425.537 °C at 760 mmHg
    3. Flash Point: 148.725 °C
    4. Appearance: /
    5. Density: 1.339 g/cm3
    6. Vapor Pressure: 0.329mmHg at 25°C
    7. Refractive Index: -22.5 ° (C=1.4, CHCl3)
    8. Storage Temp.: Refrigerator
    9. Solubility: very faint turbidity in Chloroform
    10. PKA: 12.22±0.70(Predicted)
    11. BRN: 96634
    12. CAS DataBase Reference: 1,3,4,6-TETRA-O-ACETYL-BETA-D-MANNOPYRANOSE(CAS DataBase Reference)
    13. NIST Chemistry Reference: 1,3,4,6-TETRA-O-ACETYL-BETA-D-MANNOPYRANOSE(18968-05-3)
    14. EPA Substance Registry System: 1,3,4,6-TETRA-O-ACETYL-BETA-D-MANNOPYRANOSE(18968-05-3)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: 22-24/25
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 18968-05-3(Hazardous Substances Data)

18968-05-3 Usage

Uses

Used in Pharmaceutical Industry:
1,3,4,6-TETRA-O-ACETYL-BETA-D-MANNOPYRANOSE is used as an intermediate in the preparation of precursors for the synthesis of 2-[18F]fluoro-2-deoxy-D-glucose (FDG), a radiotracer used in positron emission tomography (PET) for diagnostic purposes. FDG is commonly utilized in detecting cancerous cells, as they exhibit a higher rate of glucose metabolism compared to normal cells. The use of 1,3,4,6-TETRA-O-ACETYL-BETA-D-MANNOPYRANOSE in the synthesis of FDG precursors ensures the production of a reliable and efficient diagnostic tool for various medical applications.
Additionally, due to its unique structure and reactivity, 1,3,4,6-TETRA-O-ACETYL-BETA-D-MANNOPYRANOSE may also be employed as a building block in the development of other pharmaceutical compounds, particularly those targeting carbohydrate-based drug discovery. Its ability to form stable glycosidic linkages with various biomolecules makes it a promising candidate for the synthesis of glycoconjugates, which have potential applications in the treatment of various diseases, including cancer, infectious diseases, and inflammatory conditions.

Check Digit Verification of cas no

The CAS Registry Mumber 18968-05-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,8,9,6 and 8 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 18968-05:
(7*1)+(6*8)+(5*9)+(4*6)+(3*8)+(2*0)+(1*5)=153
153 % 10 = 3
So 18968-05-3 is a valid CAS Registry Number.
InChI:InChI=1/C9H15F7O4Si/c1-17-21(18-2,19-3)6-4-5-20-7(10,8(11,12)13)9(14,15)16/h4-6H2,1-3H3

18968-05-3 Well-known Company Product Price

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  • TCI America

  • (T1459)  1,3,4,6-Tetra-O-acetyl-β-D-mannopyranose  >97.0%(GC)

  • 18968-05-3

  • 1g

  • 1,280.00CNY

  • Detail
  • TCI America

  • (T1459)  1,3,4,6-Tetra-O-acetyl-β-D-mannopyranose  >97.0%(GC)

  • 18968-05-3

  • 5g

  • 3,950.00CNY

  • Detail

18968-05-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name [(2R,3R,4R,5S,6S)-3,4,6-triacetyloxy-5-hydroxyoxan-2-yl]methyl acetate

1.2 Other means of identification

Product number -
Other names 1,3,4,6-Tetra-O-acetyl-β-D-mannopyranose

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:18968-05-3 SDS

18968-05-3Relevant articles and documents

Disulfide dimannose-gold nanoprobe as well as preparation method and application thereof

-

Paragraph 0030-0033, (2021/03/05)

The invention belongs to the field of carbohydrate chemistry biology, and particularly relates to a disulfide dimannose-gold nanoprobe, a preparation method and application of the disulfide dimannose-gold nanoprobe in the aspect of virus receptor DC-SIGN/R recognition. The disulfide dimannose-gold nanoprobe is characterized in that a ligand exchange method is adopted, and disulfide dimannose ligands are modified on the surfaces of gold nanoparticles. The method is based on click chemistry and ligand exchange, modifies the surface of the gold nanoparticle with a mannose ligand to construct a novel dithiodimannose-gold nanoprobe, a sugar binding mechanism of tetramer lectin DC-SIGN and DC-SIGNR is researched on the basis of a fluorescence quenching strategy, and a foundation is laid for establishing a rapid and sensitive method and researching binding affinity and thermodynamics between protein-sugar multivalent interactions.

Synthesis, photophysical properties, and photodynamic activity of positional isomers of TFPP-glucose conjugates

Fadlan, Arif,Tanimoto, Hiroki,Ito, Tatsuya,Aritomi, Yusuke,Ueno, Maho,Tokuda, Masaya,Hirohara, Shiho,Obata, Makoto,Morimoto, Tsumoru,Kakiuchi, Kiyomi

, p. 1848 - 1858 (2018/03/06)

The synthesis and characterization of a ‘complete set’ of positional isomers of tetrakis(perfluorophenyl)porphyrins (TFPP)-glucose conjugates (1OH, 2OH, 3OH, 4OH, and 6OH) are reported herein. The cellular uptake and photocytotoxicity of these conjugates were examined in order to investigate the influence of location of the TFPP moiety on the D-glucose molecule on the biological activity of the conjugates. An In vitro biological evaluation revealed that the certain of these isomers have a greater effect on cellular uptake and cytotoxicity than others. The TFPP-glucose conjugates 1OH, 3OH, and 4OH were found to exert exceptional photocytotoxicity in several types of cancer cells compared to 2OH and 6OH substituted isomers.

A process for the purification of three fluorine mannose intermediate

-

Paragraph 0029, (2017/03/17)

The invention provides a method for purifying a 1,3,4,6-tetra-O-acetyl-2-O-triflat-beta-D-mannopyranose intermediate. The method comprises the following steps: adding a crude 1,3,4,6-tetraacetyl-beta-D-mannopyranose product into mixed liquid containing n-butyl alcohol and 2-methoxyethanol; heating the crude 1,3,4,6-tetraacetyl-beta-D-mannopyranose product until the crude 1,3,4,6-tetraacetyl-beta-D-mannopyranose product is dissolved; cooling the crude 1,3,4,6-tetraacetyl-beta-D-mannopyranose product until the crude 1,3,4,6-tetraacetyl-beta-D-mannopyranose product is completely crystallized; performing filtering, washing and drying to obtain the 1,3,4,6-tetra-O-acetyl-2-O-triflat-beta-D-mannopyranose intermediate, namely a 1,3,4,6-tetraacetyl-beta-D-mannopyranose crystal. The yield and purity of the 1,3,4,6-tetraacetyl-beta-D-mannopyranose are remarkably improved, so that the problems of low yield and low purity of the synthesized 1,3,4,6-tetra-O-acetyl-2-O-triflat-beta-D-mannopyranose intermediate namely 1,3,4,6-tetraacetyl-beta-D-mannopyranose in the prior art are solved.

A convenient and efficient synthetic approach to mono-, di-, and tri-O-mannosylated Fmoc amino acids

Chen, Liqun,Tan, Zhongping

, p. 2190 - 2193 (2013/04/24)

A convenient and highly efficient synthesis of mono-, di-, and tri-O-mannosylated Fmoc-Ser and Thr is described. The short synthetic route and high overall yield highlight the synthetic utility of this unified approach.

3,4,6-Tri-O-acetyl-1,2-O-[1-(exo-ethoxy)ethyl-idene]-Β-d-manno- pyranose 0.11-hydrate

Liu, Ya-Ling,Zou, Pei,Wu, Hao,Xie, Min-Hao,Luo, Shi-Neng

, p. o338-o340 (2012/11/13)

The title compound, C16H24O10·0. 11H2O, is a key inter-mediate in the synthesis of 2-de-oxy-2-[ 18F]fluoro-d-glucose (18F-FDG), which is the most widely used mol-ecular-imaging probe for positron emission tomography (PET). The crystal structure has two independent mol-ecules (A and B) in the asymmetric unit, with closely comparable geometries. The pyran-ose ring adopts a 4 C 1 conformation [Cremer-Pople puckering parameters: Q = 0.553 (2) A?, = 16.2 (2)° and = 290.4 (8)° for mol-ecule A, and Q = 0.529 (2) A?, =15.3 (3)° and = 268.2 (9)° for mol-ecule B], and the dioxolane ring adopts an envelope conformation. The chiral centre in the dioxolane ring, introduced during the synthesis of the compound, has an R configuration, with the eth-oxy group exo to the manno-pyran-ose ring. The asymmetric unit also contains one water mol-ecule with a refined site-occupancy factor of 0.222 (8), which bridges between mol-ecules A and B via O - H?O hydrogen bonds.

A biosynthetic pathway for BE-7585A, a 2-thiosugar-containing angucycline-type natural product

Sasaki, Eita,Ogasawara, Yasushi,Liu, Hung-Wen

experimental part, p. 7405 - 7417 (2010/08/05)

Sulfur is an essential element found ubiquitously in living systems. However, there exist only a few sulfur-containing sugars in nature and their biosyntheses have not been studied. BE-7585A produced by Amycolatopsis orientalis subsp. vinearia BA-07585 has a 2-thiosugar and is a member of the angucycline class of compounds. We report herein the results of our initial efforts to study the biosynthesis of BE-7585A. Spectroscopic analyses verified the structure of BE-7585A, which is closely related to rhodonocardin A. Feeding experiments using 13C-labeled acetate were carried out to confirm that the angucycline core is indeed polyketide-derived. The results indicated an unusual manner of angular tetracyclic ring construction, perhaps via a Baeyer-Villiger type rearrangement. Subsequent cloning and sequencing led to the identification of the bex gene cluster spanning ~30 kbp. A total of 28 open reading frames, which are likely involved in BE-7585A formation, were identified in the cluster. In view of the presence of a homologue of a thiazole synthase gene (thiG), bexX, in the bex cluster, the mechanism of sulfur incorporation into the 2-thiosugar moiety could resemble that found in thiamin biosynthesis. A glycosyltransferase homologue, BexG2, was heterologously expressed in Escherichia coli. The purified enzyme successfully catalyzed the coupling of 2-thioglucose 6-phoshate and UDP-glucose to produce 2-thiotrehalose 6-phosphate, which is the precursor of the disaccharide unit in BE-7585A. On the basis of these genetic and biochemical experiments, a biosynthetic pathway for BE-7585A can now be proposed. The combined results set the stage for future biochemical studies of 2-thiosugar biosynthesis and BE-7585A assembly.

Synthesis and cytotoxic properties of new fluorodeoxyglucose-coupled chlorambucil derivatives

Reux, Bastien,Weber, Valerie,Galmier, Marie-Josephe,Borel, Michele,Madesclaire, Michel,Madelmont, Jean-Claude,Debiton, Eric,Coudert, Pascal

, p. 5004 - 5020 (2008/12/21)

Frequently used in the treatment of malignant cells, alkylating agents, like most anticancer substances, produce adverse side effects caused by the toxicity of the agents toward normal tissues and lose efficiency through poor distribution to target sites.

Immunogenic glycopeptides, screening, preparation and uses

-

Page/Page column 11; sheet 7, (2008/06/13)

The invention relates to immunogenic glycopeptides derived from pathogenic microorganisms, which can be used for immunization and diagnosing infections dye to such pathogenic microorganisms and also to method for the selection and preparation thereof.

Sulfinyl hexose derivatives useful for glycosylation

-

, (2008/06/13)

Hexose derivatives are described which facilitate control over the stereochemistry of the glycosyl bond formed in the course of a solid phase glycosylation reaction. Methods for their use are also described.

Carbohydrate Homologation by the Use of 2-(Trimethylsilyl)thiazole. Preparative Scale Synthesis of Rare Sugars: L-Gulose, L-Idose, and the Disaccharide Subunit of Bleomycin A2

Dondoni, Alessandro,Marra, Alberto,Massi, Alessandro

, p. 6261 - 6267 (2007/10/03)

The well established one-carbon homologation method of protected monosaccharides employing 2-(trimethylsilyl)thiazole (2-TST) as a formyl anion equivalent has been used for high yield and multigram scale synthesis of the title rare hexoses from L-xylose. Thus, L-gulose has been obtained by stereoselective anti-addition of 2-TST to aldehydo-L-xylose diacetonide followed by thiazole to formyl conversion of the resulting alcohol. The inversion of configuration at C-1 of this alcohol by an oxidation - reduction sequence prior to the aldehyde releasing from thiazole led to L-idose. The same alcohol was readily elaborated into 1,3,4,6-tetra-O-acetyl-L-gulopyranose whose highly stereoselective glycosidation coupling with 3-O-carbamoyl-2,4,6-tri-O-acetyl-α-D-mannosyl diethyl phosphate afforded the same peracetylated disaccharide subunit employed by Boger and Honda in the total synthesis of the antibiotic bleomycin A2.

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