Welcome to LookChem.com Sign In|Join Free

CAS

  • or
1-thio-beta-D-glucose pentaacetate is a chemical compound derived from glucose that has been modified to include a thio group and five acetate groups. It is a versatile synthetic precursor in organic and biochemistry research, used for studying the reactivity and properties of carbohydrates. Its unique structure makes it a valuable building block for the synthesis of complex carbohydrates and other sugar derivatives, with potential applications in drug development and fields where carbohydrate chemistry is crucial.

13639-50-4 Suppliers

Post Buying Request

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier
  • 13639-50-4 Structure
  • Basic information

    1. Product Name: 1-thio-beta-D-glucose pentaacetate
    2. Synonyms: 1-(Acetylthio)-1-deoxy-β-D-glucopyranose tetraacetate;1-S-Acetyl-2-O,3-O,4-O,6-O-tetraacetyl-1-thio-β-D-glucopyranose;1-Thio-β-D-glucopyranose 1,2,3,4,6-pentaacetate;1-Thio-β-D-glucopyranose pentaacetate;Acetyl 2-O,3-O,4-O,6-O-tetraacetyl-1-thio-β-D-glucopyranoside;Thioacetic acid S-(2-O,3-O,4-O,6-O-tetraacetyl-β-D-glucopyranosyl) ester;Nsc409737;1-thio-beta-D-glucose pentaacetate
    3. CAS NO:13639-50-4
    4. Molecular Formula: C16H22O10S
    5. Molecular Weight: 496.48128
    6. EINECS: 237-128-3
    7. Product Categories: N/A
    8. Mol File: 13639-50-4.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 468.1°Cat760mmHg
    3. Flash Point: 222.3°C
    4. Appearance: /
    5. Density: 1.32g/cm3
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: 1-thio-beta-D-glucose pentaacetate(CAS DataBase Reference)
    10. NIST Chemistry Reference: 1-thio-beta-D-glucose pentaacetate(13639-50-4)
    11. EPA Substance Registry System: 1-thio-beta-D-glucose pentaacetate(13639-50-4)
  • 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: 13639-50-4(Hazardous Substances Data)

13639-50-4 Usage

Uses

Used in Organic Chemistry Research:
1-thio-beta-D-glucose pentaacetate is used as a synthetic precursor for studying the reactivity and properties of carbohydrates, providing insights into the behavior of modified sugar molecules in various chemical reactions.
Used in Biochemistry Research:
In biochemistry, 1-thio-beta-D-glucose pentaacetate is used as a building block for the creation of other sugar derivatives, contributing to the understanding of carbohydrate structures and their interactions with biological systems.
Used in Synthesis of Complex Carbohydrates:
1-thio-beta-D-glucose pentaacetate is utilized in the synthesis of complex carbohydrates, enabling the development of intricate sugar structures that can be used in various applications, including pharmaceuticals and materials science.
Used in Drug Development:
Due to its specific structure and reactivity, 1-thio-beta-D-glucose pentaacetate has potential applications in drug development, where it can be used to create novel carbohydrate-based therapeutic agents or to modify existing drugs to improve their efficacy and selectivity.
Used in Carbohydrate Chemistry:
In the field of carbohydrate chemistry, 1-thio-beta-D-glucose pentaacetate is employed as a key intermediate for the synthesis of various sugar derivatives, facilitating the exploration of new chemical entities and their potential applications in different industries.

Check Digit Verification of cas no

The CAS Registry Mumber 13639-50-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,6,3 and 9 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 13639-50:
(7*1)+(6*3)+(5*6)+(4*3)+(3*9)+(2*5)+(1*0)=104
104 % 10 = 4
So 13639-50-4 is a valid CAS Registry Number.

13639-50-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-thio-β-D-glucose pentaacetate

1.2 Other means of identification

Product number -
Other names -

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:13639-50-4 SDS

13639-50-4Relevant articles and documents

A Sweet H2S/H2O2Dual Release System and Specific Protein S-Persulfidation Mediated by Thioglucose/Glucose Oxidase

Li, Xiaolu,Ni, Xiang,Qian, Wei-Jun,Shen, Tun-Li,Xian, Ming

, p. 13325 - 13332 (2021/09/03)

H2S and H2O2 are two redox regulating molecules that play important roles in many physiological and pathological processes. While each of them has distinct biosynthetic pathways and signaling mechanisms, the crosstalk between these two species is also known to cause critical biological responses such as protein S-persulfidation. So far, many chemical tools for the studies of H2S and H2O2 have been developed, such as the donors and sensors for H2S and H2O2. However, these tools are normally targeting single species (e.g., only H2S or only H2O2). As such, the crosstalk and synergetic effects between H2S and H2O2 have hardly been studied with those tools. In this work, we report a unique H2S/H2O2 dual donor system by employing 1-thio-β-d-glucose and glucose oxidase (GOx) as the substrates. This enzymatic system can simultaneously produce H2S and H2O2 in a slow and controllable fashion, without generating any bio-unfriendly byproducts. This system was demonstrated to cause efficient S-persulfidation on proteins. In addition, we expanded the system to thiolactose and thioglucose-disulfide; therefore, additional factors (β-galactosidase and cellular reductants) could be introduced to further control the release of H2S/H2O2. This dual release system should be useful for future research on H2S and H2O2.

One pot synthesis of thio -glycosides via aziridine opening reactions

Hribernik, Nives,Tamburrini, Alice,Falletta, Ermelinda,Bernardi, Anna

supporting information, p. 233 - 247 (2021/01/14)

A one-pot aziridine opening reaction by glycosyl thiols generated in situ from the corresponding anomeric thio-acetates affords thio-glycosides with a pseudo-disaccharide structure and an N-linked tether. The scope of the one-pot aziridine opening reaction was explored on a series of mono- and disaccharides, creating a class of pseudo-glycosidic compounds with potential for further functionalization. Unexpected anomerization of glycosyl thiols was observed under the reaction conditions and the influence of temperature, base and solvent on the isomerization was investigated. Single isomers were obtained in good to acceptable yields for mannose, rhamnose and sialic acid derivatives. The class of thio-glycomimetics synthesized can potentially be recognized by various lectins, while presenting hydrolytic and enzymatic stability. The nitrogen functionality incorporated in the glycomimetics can be exploited for further functionalization, including tethering to linkers, scaffolds or peptide residues.

Modular Synthesis of Aryl Thio/Selenoglycosides via the Catellani Strategy

Ding, Ya-Nan,Huang, Yan-Chong,Shi, Wei-Yu,Zheng, Nian,Wang, Cui-Tian,Chen, Xi,An, Yang,Zhang, Zhe,Liang, Yong-Min

supporting information, p. 5641 - 5646 (2021/08/01)

We described a novel palladium-catalyzed domino procedure for the preparation of (hetero)aryl thio/selenoglycosides. Readily available (hetero)aryl iodides and easily accessible 1-thiosugars/1-selenosugars are utilized as the substrates. Meanwhile, 10 types of sugars are quite compatible with this reaction with good regio- and stereoselectivity, high efficiency, and broad applicability (up to 89%, 53 examples). This method enables the straightforward formation of the C(sp2)-S/Se bond of (hetero)aryl thio/selenoglycosides.

Improved Synthesis of 1-Glycosyl Thioacetates and Its Application in the Synthesis of Thioglucoside Gliflozin Analogues

Dong, Hai,Feng, Guang-Jing,Luo, tao,Lv, Jian,Wang, Shuang-Shuang,Wu, Yuzhou

, p. 2940 - 2949 (2021/07/26)

An improved method to synthesize 1-glycosyl thioacetates was developed, where per-O-acetylated glycoses were allowed to directly react with potassium thioacetate (KSAc) in the presence of BF3 ? Et2O in ethyl acetate under mild conditions. This method not only overcomes the disadvantage of the traditional one-step method, which is that the odorous and toxic thioacetic acid has to be used, but also overcomes the disadvantage of the traditional two-step method, which is that the unstable intermediate, glycosyl halide, has to be synthesized from the per-O-acetylated glycose in advance. Based on this, the per-O-acetylated glucosyl disulfide and the per-O-acetylated glucosyl 1-thiol were efficiently synthesized in high yields (91 % and 90 % respectively) starting from per-O-acetylated glycoses in two-step without the need to isolate intermediate products. Through metal-catalyzed cross-coupling of per-O-acetylated glucosyl 1-thiol with aryl-iodide under very mild conditions, two thioglucoside gliflozin analogues were efficiently synthesized in high yields for the first time. These two thioglucoside gliflozin analogues were further confirmed to be stable to hydrolysis of β-glucosidase.

Preparation method and application of peracetyl-protected 1-thioglucose and glucose 1-mercaptan

-

Paragraph 0042-0046; 0050-0059, (2021/03/24)

The invention belongs to the technical field of medicine and sugar chemical synthesis, and particularly relates to a preparation method and application of peracetyl-protected 1-thioglucose and glucose1-mercaptan. The preparation method comprises the following steps of reacting peracetyl-protected glucose and potassium thioacetate in an organic solvent at the temperature of between normal temperature and 50 DEG C under the catalysis of boron trifluoride diethyl ether for 4-8 hours to obtain peracetyl-protected 1-thioglucose; and dissolving the prepared peracetyl-protected 1-thioglucose in dimethylformamide, and removing thioacetyl by using hydrazine hydrate to obtain peracetyl-protected glucose 1-mercaptan. The peracetyl-protected glucose 1-mercaptan can be used for further preparing auronofen and gliclazide thioglycoside analogues. The method disclosed by the invention is mild in reaction condition, simple and convenient to operate, low in synthesis cost, relatively green and high inyield, the auronofen is a medicine for treating rheumatic arthritis, and the gliflozin thioglycoside analogue is a potential medicine for treating type 2 diabetes mellitus.

Efficient generation of thiolate sugars from glycosyl Bunte salts and its application to S-glycoside synthesis

Meguro, Yasuhiro,Noguchi, Masato,Li, Gefei,Shoda, Shin-ichiro

, (2020/07/20)

A one-pot aqueous solution method for synthesis of S-glycoside derivatives has been developed. Firstly, unprotected sugars were converted into glycosyl Bunte salts from which thiolate sugars can be generated efficiently using Na2S. The subsequent addition reaction with vinyl compounds or organic halides has successfully been demonstrated, giving rise to the corresponding S-glycosides.

Synthesis and Structure-Activity Relationship Study of Antimicrobial Auranofin against ESKAPE Pathogens

Wu, Bin,Yang, Xiaojian,Yan, Mingdi

supporting information, p. 7751 - 7768 (2019/09/10)

Auranofin, an FDA-approved arthritis drug, has recently been repurposed as a potential antimicrobial agent; it performed well against many Gram-positive bacteria, including multidrug resistant strains. It is, however, inactive toward Gram-negative bacteria, for which we are in dire need of new therapies. In this work, 40 auranofin analogues were synthesized by varying the structures of the thiol and phosphine ligands, and their activities were tested against ESKAPE pathogens. The study identified compounds that exhibited bacterial inhibition (MIC) and killing (MBC) activities up to 65 folds higher than that of auranofin, making them effective against Gram-negative pathogens. Both thiol and the phosphine structures influence the activities of the analogues. The trimethylphosphine and triethylphosphine ligands gave the highest activities against Gram-negative and Gram-positive bacteria, respectively. Our SAR study revealed that the thiol ligand is also very important, the structure of which can modulate the activities of the AuI complexes for both Gram-negative and Gram-positive bacteria. Moreover, these analogues had mammalian cell toxicities either similar to or lower than that of auranofin.

Dehydrative Thioglycosylation of 1-Hydroxyl Glycosides Catalyzed by In Situ-Generated AlI3

Weng, Shiue-Shien,Hsieh, Kun-Yi,Zeng, Zih-Jian

, p. 464 - 473 (2017/05/19)

Thioglycosylation of 1-hydroxyl glycosides catalyzed by in situ-generated AlI3 from elemental aluminium and molecular iodine has been developed. This method provides an alternative route to access anomeric thioglycosides without the use of hazard Lewis acidic activators or per-modified activated thiol sources. The major advantages of this dehydrative procedure are environmental friendly, ease of operation, high anomeric diastereoselectivity, and mild reaction conditions.

Design, synthesis and biological evaluation of novel podophyllotoxin derivatives bearing 4β-disulfide/trisulfide bond as cytotoxic agents

Zhu, Shi-Jun,Ying, Hua-Zhou,Wu, Yan,Qiu, Ni,Liu, Tao,Yang, Bo,Dong, Xiao-Wu,Hu, Yong-Zhou

, p. 103172 - 103183 (2015/12/23)

A novel series of C-4β-disulfide/trisulfide-containing podophyllotoxin derivatives were designed, synthesized, and biologically evaluated for their cytotoxic activities against human cancer cell lines, including KB (Mouth Epidermal Carcinoma Cells) and KB/VCR (Vincristine-resistant Mouth Epidermal Carcinoma Cells). Most of these compounds exhibited promising moderate to good cytotoxic activities. In particular, some of them displayed even superior activities to that of etoposide, especially for KB/VCR cell lines, indicating that introduction of the disulfide/trisulfide moiety would be beneficial for overcoming the multi-drug resistant limitation of etoposide. Moreover, the metabolic evaluation of the most promising compound was further performed to reveal that disulfide bond can be stable in human plasma over 8 hours, indicating good potential of these compounds for in vivo anti-cancer activities.

Selective S-deacetylation inspired by native chemical ligation: practical syntheses of glycosyl thiols and drug mercapto-analogues

Shu, Penghua,Zeng, Jing,Tao, Jinyi,Zhao, Yueqi,Yao, Guangmin,Wan, Qian

supporting information, p. 2545 - 2551 (2015/04/22)

Glycosyl thiols are useful building blocks for the construction of compounds of biological and synthetic importance. Herein, we report a practical synthetic approach toward the efficient synthesis of glycosyl thiols via chemo- and regioselective S-deacetylation inspired by native chemical ligation. This strategy allows the large scale synthesis of glycosyl thiols by simple purification steps without column chromatography. In addition, deacetylation reagents (DTT) could also be recovered and regenerated by a simple process. Thiol containing taxol and artemisinin analogues were successfully prepared based on this methodology. Finally, auranofin, a glucose-based oral drug used to treat rheumatoid arthritis, was synthesized in concise steps and overall high yields.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 13639-50-4