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2873-29-2

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2873-29-2 Usage

Chemical Properties

white to off-white crystalline powder

Uses

Different sources of media describe the Uses of 2873-29-2 differently. You can refer to the following data:
1. A D-glucal derivative.
2. 3,4,6-Tri-O-acetyl-D-glucal acts as a building block for the synthesis of oligosaccharides in both solution and solid-phase. Further, it is used in the preparation of D-arabino-1,5-anhydro-2-deoxy-hex-1-enitol.

Check Digit Verification of cas no

The CAS Registry Mumber 2873-29-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,8,7 and 3 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 2873-29:
(6*2)+(5*8)+(4*7)+(3*3)+(2*2)+(1*9)=102
102 % 10 = 2
So 2873-29-2 is a valid CAS Registry Number.
InChI:InChI=1/C12H16O7/c1-7(13)17-6-11-12(19-9(3)15)10(4-5-16-11)18-8(2)14/h4-5,10-12H,6H2,1-3H3/t10-,11-,12+/m1/s1

2873-29-2 Well-known Company Product Price

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  • Alfa Aesar

  • (L14103)  3,4,6-Tri-O-acetyl-D-glucal, 98%   

  • 2873-29-2

  • 5g

  • 193.0CNY

  • Detail
  • Alfa Aesar

  • (L14103)  3,4,6-Tri-O-acetyl-D-glucal, 98%   

  • 2873-29-2

  • 25g

  • 681.0CNY

  • Detail

2873-29-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name [(2R,3S,4R)-3,4-diacetyloxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate

1.2 Other means of identification

Product number -
Other names 3,4,6-Triacetylglucal

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:2873-29-2 SDS

2873-29-2Relevant articles and documents

A new catalyst for the reductive elimination of acylated glycosyl bromides to form glycals

Stick, Robert V.,Stubbs, Keith A.,Tilbrook, D. Matthew G.,Watts, Andrew G.

, p. 83 - 85 (2002)

Ethylene-N,N′-bis(salicylideneiminato(IV)) {VO(salen)} was developed as a catalyst for the reductive elimination of acylated glycosyl bromides to form glycals. VO(salen) to be an effective catalyst for the preparation of glycals on a multi-gram scale. The catalyst was green in colour and changed to brown as the reaction progress.

-

Takiura,K.,Honda,S.

, p. 369 - 377 (1972)

-

A convenient synthesis of glycals employing in-situ generated Cp2TiCl

Hansen, Thomas,Krintel, Sussie L.,Daasbjerg, Kim,Skrydstrup, Troels

, p. 6087 - 6090 (1999)

Reductive elimination of acetylated glycosyl bromides to the corresponding glycal is easily achieved by mixing the bromide with Cp2TiCl2 and Mn in THF, and hence does not require the separate preparation of Cp2TiCl using glove-box techniques.

Long-lived glycosyl-chromium(III) complex intermediates in aqueous medium. Preparation of pyranoid glycals

Kovacs, Gyoengyver,Gyarmati, Julianna,Somsak, Laszlo,Micskei, Karoly

, p. 1293 - 1296 (1996)

Acetylated glycosyl-chromium(III)L (L=EDTA, NTA, IDA) complex intermediates (1) were detected in aqueous medium, with half-life-times of 30-300 minutes. The decay of these intermediates led to glycals (7-9) of high purity in preparatively usable 70-90% yields.

Titanium(III) reagents in carbohydrate chemistry: Glycal and C-glycoside synthesis

Spencer, Roxanne P.,Schwartz, Jeffrey

, p. 2103 - 2112 (2000)

Titanocene(III) chloride and zirconcene(III) chloride are effective and mild reagents for radical generation in organic synthesis. In carbohydrate chemistry, these species are useful for the conversion of glycosyl halides to glycals, and for the stereospecific preparation of C-glycosides. In all cases, the 1-glycosyl radical is an active intermediate, generated by reaction of carbohydrate substrates with the organometallic. (C) 2000 Elsevier Science Ltd.

Method for efficiently constructing 1, 2-cis-2-nitro-glucoside and galactoside

-

Paragraph 0038; 0062, (2021/08/11)

The invention discloses a method for efficiently constructing 1, 2-cis-2-nitro-glucoside and 1, 2-cis-2-nitro-galactoside, and belongs to the technical field of organic synthesis. According to the preparation method, the 1, 2-cis-2-nitro-glucoside and the 1, 2-cis-2-nitro-galactoside can be efficiently prepared through one-step synthesis. According to the present invention, the organic catalysis stereoselective glycosylation method is successfully applied to the sugar chemical total synthesis so that the problem of the construction of the 1, 2-cis-glucosidic bond between the most key sugar units is solved, and the foundation is established for the completion of the subsequent poly O-antigen total synthesis. The work has important reference value for related immunological research and vaccine development in the future.

Synthesis of 2′-paclitaxel 2-deoxy-2-fluoro-glucopyranosyl carbonate for specific targeted delivery to cancer cells

Li, Tingshen,Li, Xiao,Lian, Xujing,Meng, Xin,Ya, Qiang,Yang, Yang,Zhang, Yan,Zhang, Yongmin

supporting information, (2020/06/01)

A novel 2-fluorodeoxyglucose conjugated derivative of paclitaxel was efficiently synthesized using a linker between 2′-OH of paclitaxel and C1-hydroxyl group of 2-fluorodeoxyglucose. In preparation of the prodrug, allyl carbonates were selected as the protective group and the efficient one-step removal of allyloxycarbonyl groups at the end of the synthesis using palladium chemistry gave the target molecule in good yield. The prodrug not only improved the pharmaceutical properties of paclitaxel, such as solubility and stability, but also demonstrated enhanced cytotoxicity and selectivity for cancer cells and less toxicity toward normal HUVEC cells.

The synthesis of rare earth metal-doped upconversion nanoparticles coated with d-glucose or 2-deoxy-d-glucose and their evaluation for diagnosis and therapy in cancer

Sharma, K. Shitaljit,Thoh, Maikho,Dubey, Akhil K.,Phadnis, Prasad P.,Sharma, Deepak,Sandur, Santosh K.,Vatsa, Rajesh K.

, p. 13834 - 13842 (2020/09/07)

Rare earth metal-doped upconversion nanoparticles (UCNPs) are emerging as a new class of biomedical imaging materials due to their higher energy anti-Stokes shift, high optical penetration depth and long term repetitive imaging. In the present study, upconversion nanoparticles based on NaYF4 doped with thulium (Tm) and ytterbium (Yb) were prepared via a thermolysis method using oleic acid as a capping agent and 1-octadecene as a solvent. The X-ray diffraction pattern of the synthesized nanoparticles was found to match the standard hexagonal phase. The nanoparticles were coated with silica using tetraethyl orthosilicate (TEOS) and in order to avoid agglomeration, IGEPAL CO-520 was used as the surfactant. The coatings of SiO2 over NaYF4 were confirmed by the TEM image and XRD pattern. NaYF4@SiO2 was further functionalized by the addition of (3-aminopropyl)trimethoxysilane (APTMS) followed by either d-glucose or 2-deoxy-d-glucose (2-DG). UCNPs-d-glucose and UNCPs-2DG were examined for cell viability (MCF-7 cells) by MTT assay. The cellular uptake of UCNPs in MCF-7 cells was seen in terms of emission of a blue light. Furthermore, the uptake rate of UCNPs coated with 2-deoxy-d-glucose was found to be much faster than that of UCNPs alone under d-glucose starved conditions. The functionalization of UCNPs with 2-deoxy-d-glucose (2-DG) not only increased the uptake of nanoparticles, but also blocked the glycolysis pathway resulting in the inhibition of tumor growth as 2-deoxy-d-glucose (2-DG) is mimicking the d-glucose. The results are indicative that these upconversion nanoparticles may find applications in bio-imaging, removal of tumor by precision surgery, therapy and targeted drug delivery. This journal is

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