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4304-12-5,MFCD00674884
Catalog No.:AA00DFEP

4304-12-5 | Benzyl beta-d-glucopyranoside

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50mg
≥97%
in stock  
$102.00   $72.00
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250mg
≥97%
in stock  
$224.00   $157.00
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1g
≥97%
in stock  
$568.00   $398.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00DFEP
Chemical Name:
Benzyl beta-d-glucopyranoside
CAS Number:
4304-12-5
Molecular Formula:
C13H18O6
Molecular Weight:
270.2784
MDL Number:
MFCD00674884
SMILES:
OC[C@H]1O[C@@H](OCc2ccccc2)[C@@H]([C@H]([C@@H]1O)O)O
Properties
Computed Properties
 
Complexity:
268  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
4  
XLogP3:
-0.7  

Downstream Synthesis Route
1125-88-8    4304-12-5   
benzyl4,6-O-benzylidene-β-D-glucopyranoside 

[1]Zheng,Shaojun;Laraia,Luca;O'Connor,CorneliusJ.;Sorrell,David;Tan,YawSing;Xu,Zhaochao;Venkitaraman,AshokR.;Wu,Wenjun;Spring,DavidR.[OrganicandBiomolecularChemistry,2012,vol.10,#13,p.2590-2593]

[2]Matović,Jelena;Järvinen,Juulia;Sokka,IrisK.;Imlimthan,Surachet;Raitanen,Jan-Erik;Montaser,Ahmed;Maaheimo,Hannu;Huttunen,KristiinaM.;Peräniemi,Sirpa;Airaksinen,AnuJ.;Sarparanta,Mirkka;Johansson,MikaelP.;Rautio,Jarkko;Ekholm,FilipS.[MolecularPharmaceutics,2021,vol.18,#1,p.285-304]

[3]Sarkar,SujitKumar;Choudhury,AmbarKumar;Mukhopadhyay,Balaram;Roy,Nirmolendu[JournalofCarbohydrateChemistry,1999,vol.18,#9,p.1121-1130]

[4]CurrentPatentAssignee:IOWASTATEUNIVERSITYOFSCIENCEANDTECHNOLOGY;THEUNIVERSITYOFIOWA-US2013/252909,2013,A1Locationinpatent:Paragraph0027

[5]Patra,Malay;Awuah,SamuelG.;Lippard,StephenJ.[JournaloftheAmericanChemicalSociety,2016,vol.138,#38,p.12541-12551]

14602-86-9    4304-12-5   
benzyl6-O-menthyloxycarbonyl-β-D-glucopyranoside 

[1]CurrentPatentAssignee:ALTRIAGROUPINC;PHILIPMORRISINTERNATIONALINC.-US5139034,1992,A

Literature

Title: Structure-activity relationship studies of 4-benzyl-1H-pyrazol-3-yl β-d-glucopyranoside derivatives as potent and selective sodium glucose co-transporter 1 (SGLT1) inhibitors with therapeutic activity on postprandial hyperglycemia.

Journal: Bioorganic & medicinal chemistry 20121115

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Engineering of glucoside acceptors for the regioselective synthesis of beta-(1-->3)-disaccharides with glycosynthases.

Journal: Carbohydrate research 20081124

Title: Chemoenzymatic synthesis of naturally occurring benzyl 6-O-glycosyl-beta-D-glucopyranosides.

Journal: Chemical & pharmaceutical bulletin 20050801

Title: Intestinal SGLT1-mediated absorption and metabolism of benzyl beta-glucoside contained in Prunus mume: carrier-mediated transport increases intestinal availability.

Journal: Biochimica et biophysica acta 20050311

Title: Effects of benzyl glucoside and chlorogenic acid from Prunus mume on adrenocorticotropic hormone (ACTH) and catecholamine levels in plasma of experimental menopausal model rats.

Journal: Biological & pharmaceutical bulletin 20040101

Title: A new pyrroloquinazoline alkaloid from Linaria vulgaris.

Journal: Chemical & pharmaceutical bulletin 20021001

Title: Natural glycosides containing allopyranose from the passion fruit plant and circular dichroism of benzaldehyde cyanohydrin glycosides.

Journal: Organic letters 20010712

Title: Studies on antiviral glycosides. Synthesis and biological evaluation of various phenyl glycosides.

Journal: Carbohydrate research 19780401

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