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.alpha.-D-Mannopyranose, 2,3,4,6-tetrabenzoate 1-(2,2,2-trichloroethanimidate) is a complex organic compound derived from the sugar D-Mannose. It is characterized by the presence of four benzoyl groups attached to the hydroxyl groups at positions 2, 3, 4, and 6 of the mannopyranose ring, and a 2,2,2-trichloroethanimidate group at the anomeric position 1. .alpha.-D-Mannopyranose, 2,3,4,6-tetrabenzoate 1-(2,2,2-trichloroethanimidate) is known for its potential applications in various fields, particularly in the synthesis of mannosyl-based dendrimers and as an inhibitor for treating microbial infections.

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  • .alpha.-D-Mannopyranose, 2,3,4,6-tetrabenzoate 1-(2,2,2-trichloroethanimidate)

    Cas No: 183901-63-5

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  • 183901-63-5 Structure
  • Basic information

    1. Product Name: .alpha.-D-Mannopyranose, 2,3,4,6-tetrabenzoate 1-(2,2,2-trichloroethanimidate)
    2. Synonyms: .alpha.-D-Mannopyranose, 2,3,4,6-tetrabenzoate 1-(2,2,2-trichloroethanimidate);2,3,4,6-Tetra-O-benzoyl-α-D-Mannopyranosyl TrichloroacetiMidate
    3. CAS NO:183901-63-5
    4. Molecular Formula: C36H28Cl3NO10
    5. Molecular Weight: 740.97
    6. EINECS: N/A
    7. Product Categories: Carbohydrates & Derivatives
    8. Mol File: 183901-63-5.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: .alpha.-D-Mannopyranose, 2,3,4,6-tetrabenzoate 1-(2,2,2-trichloroethanimidate)(CAS DataBase Reference)
    10. NIST Chemistry Reference: .alpha.-D-Mannopyranose, 2,3,4,6-tetrabenzoate 1-(2,2,2-trichloroethanimidate)(183901-63-5)
    11. EPA Substance Registry System: .alpha.-D-Mannopyranose, 2,3,4,6-tetrabenzoate 1-(2,2,2-trichloroethanimidate)(183901-63-5)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 183901-63-5(Hazardous Substances Data)

183901-63-5 Usage

Uses

Used in Pharmaceutical Industry:
.alpha.-D-Mannopyranose, 2,3,4,6-tetrabenzoate 1-(2,2,2-trichloroethanimidate) is used as a key intermediate in the synthesis of mannosyl-based dendrimers. These dendrimers are multi-branched, nano-scale polymers that can be employed as drug delivery systems, enhancing the solubility, stability, and bioavailability of various therapeutic agents. The unique structure of these dendrimers allows for the precise control of their size, shape, and surface properties, making them versatile platforms for drug development.
Used in Antimicrobial Applications:
.alpha.-D-Mannopyranose, 2,3,4,6-tetrabenzoate 1-(2,2,2-trichloroethanimidate) is also used as an inhibitor for treating microbial infections. .alpha.-D-Mannopyranose, 2,3,4,6-tetrabenzoate 1-(2,2,2-trichloroethanimidate) can interfere with the biosynthesis of bacterial cell walls, specifically targeting the enzymes involved in the synthesis of peptidoglycan, a major component of the cell wall. By inhibiting this process, the compound can effectively disrupt the structural integrity of bacterial cells, leading to their death and preventing the spread of infections.

Check Digit Verification of cas no

The CAS Registry Mumber 183901-63-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,8,3,9,0 and 1 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 183901-63:
(8*1)+(7*8)+(6*3)+(5*9)+(4*0)+(3*1)+(2*6)+(1*3)=145
145 % 10 = 5
So 183901-63-5 is a valid CAS Registry Number.

183901-63-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl Trichloroacetimidate

1.2 Other means of identification

Product number -
Other names [(2R,3R,4S,5S,6R)-3,4,5-tribenzoyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl benzoate

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:183901-63-5 SDS

183901-63-5Relevant articles and documents

Oligomannoside mimetics by glycosylation of 'octopus glycosides' and their investigation as inhibitors of type 1 fimbriae-mediated adhesion of Escherichia coli

Dubber, Michael,Sperling, Oliver,Lindhorst, Thisbe K.

, p. 3901 - 3912 (2006)

The glycocalyx of eukaryotic cells is composed of glycoconjugates, which carry highly complex oligosaccharide portions. To elucidate the biological role and function of the glycocalyx in cell-cell communication and cellular adhesion processes, glycomimeti

New lipophilic glycomimetic DC-SIGN ligands: Stereoselective synthesis and SPR-based binding inhibition assays

Di Pietro, Sebastiano,Bordoni, Vittorio,Iacopini, Dalila,Achilli, Silvia,Pineschi, Mauro,Thépaut, Michel,Fieschi, Franck,Crotti, Paolo,Di Bussolo, Valeria

, (2021)

The design and synthesis of efficient ligands for DC-SIGN is a topic of high interest, because this C-type lectin has been implicated in the early stages of many infection processes. DC-SIGN membrane-protein presents four carbohydrate-binding domains (CRD) that specifically recognize mannose and fucose. Therefore, antagonists of minimal disaccharide epitope Manα(1,2)Man, represent potentially interesting antibacterial and antiviral agents. In the recent past, we were able to develop efficient antagonists, mimics of the natural moiety, characterized by the presence of a real D-carbamannose unit which confers greater stability to enzymatic breakdown than the corresponding natural disaccharide ligand. Herein, we present the challenging stereoselective synthesis of four new amino or azide glycomimetic DC-SIGN antagonists with attractive orthogonal lipophilic substituents in C(3), C(4) or C(6) positions of the real carba unit, which were expected to establish crucial interactions with lipophilic areas of DC-SIGN CRD. The activity of the new ligands was evaluated by SPR binding inhibition assays. The interesting results obtained, allow to acquire important information about the influence of the lipophilic substituents present in specific positions of the carba scaffold. Furthermore, C(6) benzyl C(4) tosylamide pseudodisaccharide displayed a good affinity for DC-SIGN with a more favorable IC50 value than those of the previously described real carba-analogues. This study provides valuable knowledge for the implementation of further structural modifications towards improved inhibitors.

Synthesis of Carbohydrate-Centered Oligosaccharide Mimetics Equipped with a Functionalized Tether

Dubber, Michael,Lindhorst, Thisbe K.

, p. 5275 - 5281 (2000)

Synthetic glycoclusters have gained substantial attention as mimetics of multivalent glycoconjugates. For their proposed glycobiological applications, it is advantageous to incorporate a functionalized tether into the clusters, which allows coupling to so

Synthesis of a Glycosylphosphatidylinositol (GPI) Fragment as a Potential Substrate for Mannoprotein Transglycosidases

Belz, Tyson F.,Williams, Spencer J.

, p. 2053 - 2058 (2021/08/31)

A glycophosphatidylinositol tetrasaccharide fragment was synthesized to mimic the core features of primary model, that of Saccharomyces cerevisiae. The salient feature of this approach is centered on the quick access to various α-1,2- and α-1,6-mannosyl a

Carbon tetrachloride-free allylic halogenation-mediated glycosylations of allyl glycosides

Das, Anupama,Jayaraman, Narayanaswamy

, p. 9318 - 9325 (2021/11/13)

The allylic bromination of allyl glycosides is conducted using NBS/AIBN reagents in (EtO)2CO and PhCF3 solutions, without using CCl4 as a solvent. The activated mixed halo-allyl glycosides led to glycosylations, mediated by a triflate, in a latent-active

GLUCOSE-RESPONSIVE INSULIN CONJUGATES

-

, (2021/02/05)

Glucose-responsive insulin conjugates that contain one or more trisaccharides are provided. Such insulin conjugates may display a pharmacokinetic (PK) and/or pharmacodynamic (PD) profile that is responsive to the systemic concentrations of a saccharide such as glucose or alpha-methylmannose, even when administered to a subject in need thereof in the absence of an exogenous multivalent saccharide-binding molecule.

36 branchings honeydews five sugar six sugar-to methoxyphenyl glycoside and its preparation method and application

-

Paragraph 0070-0072, (2017/09/19)

The invention provides a 3,6-branched mannopentaose and hexaose on methoxy phenyl glycoside and a preparation method and an application thereof. A structural formula is shown in a formula I or a formula II; a compound can be used for preparing anti-HIV me

The dehydroepiandrosterone and dehydroepiandrosterone alkone glycosylation derivative and its preparation method and application

-

Paragraph 0041; 0050; 0051, (2017/04/28)

The invention discloses epiandrosterone glycosylation derivatives and dehydrogenated epiandrosterone glycosylation derivatives, and a preparation method thereof. The preparation method comprises the following steps: respectively carrying out coupling reac

3 - monosaccharide acid oxygen glucoside oleanolic alkane type and wusu alkane triterpene saponin derivative and its preparation method and application

-

Paragraph 0035; 0039; 0113, (2017/08/25)

The invention discloses a 3-monouronic acid o-glycoside oleanane type and ursane type triterpenoid saponin derivative. The derivative has a structural formula as shown in the specification, wherein R4 is one of H atom, alkyl containing 1-10 carbons, alkyl

Cross metathesis assisted solid-phase synthesis of glycopeptoids

Khan, Sharaf Nawaz,Kim, Arim,Grubbs, Robert H.,Kwon, Yong-Uk

, p. 2952 - 2955 (2012/07/30)

A solid-phase synthesis of glycopeptoids was explored through olefin cross metathesis (CM). Peptoids and sugar derivatives with appropriate olefin moieties were coupled in the presence of an olefin metathesis catalyst to afford glycopeptoids in good yield

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