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Allyl 4,6-O-benzylidene-alpha-D-glucopyranoside is a chemical compound with the molecular formula C17H20O6, derived from glucose and classified as a glycoside. It is characterized by its potential applications in organic synthesis, pharmaceutical development, and as a reagent in chemical reactions. Its biological activities, such as antiviral, anticancer, and anti-inflammatory properties, highlight its value in medicinal and pharmaceutical applications.

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  • 20746-64-9 Structure
  • Basic information

    1. Product Name: Allyl 4,6-O-benzylidene-alpha-D-glucopyranoside
    2. Synonyms: Allyl 4,6-O-benzylidene-alpha-D-glucopyranoside;Allyl 4,6-O-benzylidene-a-D-galactopyranoside;Allyl4,6-O-benzylidene-a-D-glucopyranoside;Allyl-4,6-O-benzylidene-α-D-glucopyranoside;Allyl 4,6-O-benzylidene-α-D-galactopyranoside;2-Propenyl 4,6-O-(phenylmethylene)-alpha-D-galactopyranoside;a-D-Galactopyranoside,2-propenyl 4,6-O-(phenylmethylene)- (9CI)
    3. CAS NO:20746-64-9
    4. Molecular Formula: C16H20O6
    5. Molecular Weight: 308.3264
    6. EINECS: 1533716-785-6
    7. Product Categories: N/A
    8. Mol File: 20746-64-9.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: Allyl 4,6-O-benzylidene-alpha-D-glucopyranoside(CAS DataBase Reference)
    10. NIST Chemistry Reference: Allyl 4,6-O-benzylidene-alpha-D-glucopyranoside(20746-64-9)
    11. EPA Substance Registry System: Allyl 4,6-O-benzylidene-alpha-D-glucopyranoside(20746-64-9)
  • 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: 20746-64-9(Hazardous Substances Data)

20746-64-9 Usage

Uses

Used in Organic Synthesis:
Allyl 4,6-O-benzylidene-alpha-D-glucopyranoside is used as a reagent in organic synthesis for its ability to facilitate various chemical reactions, contributing to the creation of new compounds and materials.
Used in Pharmaceutical Development:
In the pharmaceutical industry, Allyl 4,6-O-benzylidene-alpha-D-glucopyranoside is used as a precursor in the development of new drugs due to its potential biological activities, which include antiviral, anticancer, and anti-inflammatory effects.
Used in Bioactive Compounds Research:
Allyl 4,6-O-benzylidene-alpha-D-glucopyranoside is utilized in research for the discovery and development of bioactive compounds, given its demonstrated potential to exhibit therapeutic properties beneficial for human health.

Check Digit Verification of cas no

The CAS Registry Mumber 20746-64-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,0,7,4 and 6 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 20746-64:
(7*2)+(6*0)+(5*7)+(4*4)+(3*6)+(2*6)+(1*4)=99
99 % 10 = 9
So 20746-64-9 is a valid CAS Registry Number.

20746-64-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-phenyl-6-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol

1.2 Other means of identification

Product number -
Other names Allyl-4,6-O-benzylidene-a-D-glucopyranoside

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:20746-64-9 SDS

20746-64-9Relevant articles and documents

A Synthetic Carbohydrate-Protein Conjugate Vaccine Candidate against Klebsiella pneumoniae Serotype K2

Ravinder, Mettu,Liao, Kuo-Shiang,Cheng, Yang-Yu,Pawar, Sujeet,Lin, Tzu-Lung,Wang, Jin-Town,Wu, Chung-Yi

, p. 15964 - 15997 (2020/11/13)

Klebsiella pneumoniae causes pneumonia and liver abscesses in humans worldwide and contains virulence factor capsular polysaccharides and lipopolysaccharides linked to the cell wall. Although capsular polysaccharides are good antigens for vaccine producti

Preparation method of fondaparinux sodium disaccharide intermediate

-

Paragraph 0053; 0054; 0057; 0058, (2020/02/19)

The invention discloses a preparation method of fondaparinux sodium disaccharide intermediate. 1-O-substituent sulfonyl-2,3-bis-O-benzyl-4,6-O-benzylidene-beta-D-glucopyranose directly reacts with 1,6-dehydrated-2-deoxy-2-azido-3-O-acetyl-beta-D-glucopyranose to prepare the fondaparinux sodium disaccharide intermediate as shown in a formula I; and meanwhile, the fondaparinux sodium intermediate asshown in the formula I can be used as a raw material to synthesize fondaparinux sodium intermediate as shown in a formula IV. The preparation method is simple and small in steps, the yield is high, the atomic utilization rate is high, the three wastes are small, and the preparation method is suitable for industrial large-scale production. Please see the description for the formula.

5,5-Difluoro- and 5-Fluoro-5-methyl-hexose-based C-Glucosides as potent and orally bioavailable SGLT1 and SGLT2 dual inhibitors

Demarest, Keith,Du, Fuyong,Gaul, Michael D.,Kuo, Gee-Hong,Liang, Yin,Xu, Guozhang,Xu, June Zhi

, (2020/07/21)

(2S,3R,4R,5S,6R)-2-Aryl-5,5-difluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diols and (2S,3R,4R,5S,6R)-2-aryl-5-fluoro-5-methyl-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diols were discovered as dual inhibitors of sodium glucose co-transporter proteins (

5,5-DIFLUORO- AND 5-FLUORO-5-METHYL-C-GLYCOSIDE DERIVATIVES USEFUL AS DUAL SGLT1 / SGLT2 MODULATORS

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Page/Page column 76; 79-80, (2019/11/28)

The present invention is directed to 5,5-difluoro- and 5-fluoro-5-methyl-C-glycoside derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by SGLT activity, more particularly dual SGLT1/2 activity.

BENZOCYCLOBUTANE DERIVATIVES USEFUL AS DUAL SGLT1/SGLT2 MODULATORS

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Page/Page column 58; 59, (2018/05/27)

The present invention is directed to benzocyclobutane derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by SGLT activity, more particularly dual SGLT1/2 activity. More particularly, the compounds of the present invention are useful in the treatment of for example, Type II diabetes mellitus, Syndrome X, and complications and symptoms associated with said disorders.

Three Solvent-Free Catalytic Approaches to the Acetal Functionalization of Carbohydrates and Their Applicability to One-Pot Generation of Orthogonally Protected Building Blocks

Traboni, Serena,Bedini, Emiliano,Giordano, Maddalena,Iadonisi, Alfonso

, p. 3562 - 3572 (2016/01/25)

Three alternative protocols were developed to carry out the selective installation of acetal groups on carbohydrates and polyols under mildly acidic, solvent-free conditions. One protocol is based on a diol/aldehyde condensation at room temperature, with an acetolysis process serving for the activation of the carbonyl component. A second approach is based on an orthoester-mediated activation of the carbonyl component at high temperature. The third protocol is instead entailing a transacetalation mechanism. Combination of these methods allows a wide set of acetal-protected building blocks to be accessed in short times under very simple experimental conditions working under air. The scope of the latter two approaches was also extended to unusual one-pot synthetic sequences leading to concomitant Fischer glycosidation/acetal protection of reducing sugars.

2,4,6-Trichloro-1,3,5-triazine (TCT) mediated one-pot sequential functionalisation of glycosides for the generation of orthogonally protected monosaccharide building blocks

Tatina, Madhubabu,Yousuf, Syed Khalid,Mukherjee, Debaraj

supporting information; experimental part, p. 5357 - 5360 (2012/07/30)

Orthogonally protected monosaccharide building blocks have been prepared using TCT in a one-pot multicomponent transformation. The process involves successive steps of arylidene acetalation, esterification and regioselective reductive acetal cleavage. High regioselectivity, scope for using a broad range of substrates, functional group tolerance, mild reaction conditions, easy handling process and wide application range are a few advantages of the current process.

Stereoselective dihydroxylation reaction of alkenyl β- D -hexopyranosides: A methodology for the synthesis of glycosylglycerol derivatives and 1-O-Acyl-3-O-β- D -glycosyl-sn-glycerol analogues

Vega-Perez, Jose M.,Palo-Nieto, Carlos,Perinan, Ignacio,Vega-Holm, Margarita,Calderon-Montano, Jose M.,Lopez-Lazaro, Miguel,Iglesias-Guerra, Fernando

experimental part, p. 1237 - 1252 (2012/04/10)

A variety of new glycosylglycerol derivatives have been prepared by stereoselective dihydroxylation of a range of alkenyl β-D-hexopyanosides under Donohoe's conditions. We have studied the relationship between the diastereoisomeric excess and the structural features of the precursor (sugar and alkenyl moieties). The stereochemical yields demonstrated that the presence of a hydrogen-bond donor group (OH, NHAc) at the 2-position of the sugar moiety is required to obtain high levels of stereofacial discrimination. New 1-O-acyl-3-O-β-D-glycosyl-sn-glycerol analogues were obtained by functionalisation of the primary hydroxy group with a fatty acid. Preliminary cytotoxic activity assays of both glycosylglycerol and glycoglycerolipid analogues are also presented. An efficient asymmetric dihydroxylation reaction of alkenyl β-D-hexopyranoside derivatives is described. New glycosylglycerol and glycoglycerolipid analogues have been synthesised by this methodology. Preliminary cytotoxic activity assays are presented. Copyright

COMPOUND RETAINED IN TUMOR

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Page/Page column 48, (2011/12/03)

A novel compound which specifically resides in a tumor, a method for allowing it to reside in a tumor, and a method for detecting, diagnosing, and treating tumor with use thereof are provided. The present invention relates to a compound represented by chemical formula (I) wherein R is an anionic group binding to hydrogen, R1 is OH, OCOH, OCO(CH2)hCH3, or an acting group, h being an integer of 0 or more, R2 is H, OH, OCOH, OCO(CH2)iCH3, or an acting group, i being an integer of 0 or more, R3 is OH, SO3H, or an acting group, R4 is OH, SO3H, or an acting group, and R5 is OH, SO3H, or an acting group, at least one of R1, R2, R3, R4, and R5 containing an acting group, or pharmaceutically acceptable salts thereof.

Total synthesis of 3,3-difluorinated 1-deoxynojirimycin analogues

Csuk, René,Prell, Erik,Korb, Claudia,Kluge, Ralph,Str?hl, Dieter

experimental part, p. 467 - 472 (2010/04/04)

Difluorination of 1-deoxynojirimycin at position C(3) creates a competitive inhibitor 15 of 10 times higher activity against an α-glucosidase than the parent compound. Its screening against a panel of human cell lines showed a low cytotoxicity therefore m

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