Cas 191165-25-0,ethyl 2,3,4,6-tetra-O-benzyl-D-gluconate

191165-25-0

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Basic information

Product Name: ethyl 2,3,4,6-tetra-O-benzyl-D-gluconate
Synonyms: ethyl 2,3,4,6-tetra-O-benzyl-D-gluconate
CAS NO:191165-25-0
Molecular Formula:
Molecular Weight: 584.709
EINECS: N/A
Product Categories: N/A

Chemical Properties

Melting Point: N/A
Boiling Point: N/A
Flash Point: N/A
Appearance: N/A
Density: N/A
Refractive Index: N/A
Storage Temp.: N/A
Solubility: N/A
CAS DataBase Reference: ethyl 2,3,4,6-tetra-O-benzyl-D-gluconate(CAS DataBase Reference)
NIST Chemistry Reference: ethyl 2,3,4,6-tetra-O-benzyl-D-gluconate(191165-25-0)
EPA Substance Registry System: ethyl 2,3,4,6-tetra-O-benzyl-D-gluconate(191165-25-0)

Safety Data

Hazard Codes: N/A
Statements: N/A
Safety Statements: N/A
WGK Germany:
RTECS:
HazardClass: N/A
PackingGroup: N/A
Hazardous Substances Data: 191165-25-0(Hazardous Substances Data)

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Check Digit Verification of cas no

The CAS Registry Mumber 191165-25-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,9,1,1,6 and 5 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 191165-25:
(8*1)+(7*9)+(6*1)+(5*1)+(4*6)+(3*5)+(2*2)+(1*5)=130
130 % 10 = 0
So 191165-25-0 is a valid CAS Registry Number.

191165-25-0Upstream product

191165-25-0Downstream Products

1006590-18-6 2-(2H)-2,3,4,6-tetra-O-benzyl-D-glucono-1,5-lactone

191165-25-0Relevant academic research and scientific papers

C-2 Epimerization of aldonolactones promoted by magnesium iodide: a new way towards non-enzymatic epimerization

Gratien, Julie,Heck, Marie-Pierre,Mioskowski, Charles

, p. 18 - 30 (2008/09/18)

The first example of a non-enzymatic C-2 epimerization of aldonolactones is reported. The reaction of 2,3,4,6-tetra-O-benzyl-d-gluconolactone or 2,3,4,6-tetra-O-benzyl-d-mannonolactone with MgI2 in EtOH afforded their respective C-2 epimer. Studies conducted in EtOD showing the incorporation of a deuterium atom only at the C-2 position of the epimerized product reveal an epimerization rather than a racemization reaction. A mechanism involving a chelation with a magnesium species is proposed to explain this C-2 inversion reaction.

An efficient activation of the hydroxyl function by (diethylamino)sulfur trifluoride (DAST): preparation of chiral polyoxygenated tetrahydrofurans by stereoselective benzyloxy group participation

Monthiller, Sophie,Heck, Marie-Pierre,Mioskowski, Charles,Lafargue, Pierre,Lellouche, Jean-Paul,Masella, Michel

, p. 145 - 152 (2007/10/03)

Based on an intramolecular benzyloxy or amide group participation, two sets of experimental conditions have been established for the preparation of cis/trans tetrahydrofurans 6 or lactone 8 from sugar-derived open-chain hydroxylated precursors 4.These include: (1) a two-step mesylation-cyclization promoted by LiOH/THF-H2O or NaI/CH3CN at reflux; or (2) a one-step cyclization mediated by (diethylamino)sulfur trifluoride (DAST) at -78 deg C in CH2Cl2.The scope and limitations of these cyclizations are described particularly in relation to a stereoselective synthesis of highly oxygenated chiral tetrahydrofurans.Molecular modeling studies tentatively rationalized our experimental cyclization results affording five-membered versus six-membered heterocycles starting from different precursors. - Keywords: polyoxygenated tetrahydrofuran; (diethylamino)sulfur trifluoride (DAST); benzyl group participation; amide group participation; L-gulonolactone; differentially protected 1,4-diol

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