beta-D-Glucopyranoside, ethyl, tetraacetate

Base Information

• Chemical Name: beta-D-Glucopyranoside, ethyl, tetraacetate
• CAS No.: 6697-87-6
• Molecular Formula: C₁₆H₂₄O₁₀
• Molecular Weight: 376.361
• NSC Number: 170156
• DSSTox Substance ID: DTXSID00305305

Synonyms:NSC170156;6697-87-6;SCHEMBL22201507;DTXSID00305305;NSC-170156

Chemical Property of beta-D-Glucopyranoside, ethyl, tetraacetate

Chemical Property:

• Vapor Pressure: 2.7E-07mmHg at 25°C
• Boiling Point: 421°C at 760 mmHg
• Flash Point: 181.5°C
• PSA: 123.66000
• Density: 1.24g/cm³
• LogP: 0.10600
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 11
• Exact Mass: 376.13694696
• Heavy Atom Count: 26
• Complexity: 531

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1C(C(C(C(O1)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of beta-D-Glucopyranoside, ethyl, tetraacetate

There total 2 articles about beta-D-Glucopyranoside, ethyl, tetraacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

acetic anhydride (108-24-7) + ethyl α-D-glucopyranoside (3198-49-0,15486-24-5,18997-88-1,19467-01-7,34625-23-5,59121-69-6,118245-31-1,118245-32-2,142925-34-6) → ethyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside (6697-87-6,15486-25-6,31281-90-0,53716-95-3,73098-12-1,75860-68-3,75860-69-4,101626-94-2,110456-49-0)

Guidance literature:

In pyridine; Yield given;

Reference yield:

acetic anhydride (108-24-7) + (2R,3R,4S,5S,6R)-2-Ethoxy-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (3198-49-0,15486-24-5,18997-88-1,19467-01-7,34625-23-5,59121-69-6,118245-31-1,118245-32-2,142925-34-6) → ethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (6697-87-6,15486-25-6,31281-90-0,53716-95-3,73098-12-1,75860-68-3,75860-69-4,101626-94-2,110456-49-0)

Guidance literature:

With pyridine; for 3.5h; Ambient temperature;

DOI:10.1016/0031-9422(95)00398-Q

Reference yield:

ethyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside (6697-87-6,15486-25-6,31281-90-0,53716-95-3,73098-12-1,75860-68-3,75860-69-4,101626-94-2,110456-49-0) → ethyl α-D-glucopyranoside (3198-49-0,15486-24-5,18997-88-1,19467-01-7,34625-23-5,59121-69-6,118245-31-1,118245-32-2,142925-34-6)

Guidance literature:

With ethanol; sodium ethanolate;

DOI:10.1021/ja01349a037

upstream raw materials:

acetic anhydride

(2R,3R,4S,5S,6R)-2-Ethoxy-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

ethyl α-D-glucopyranoside

Downstream raw materials:

(2R,3R,4S,5S,6R)-2-Ethoxy-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Dodecanoic acid (2R,3R,4S,5S,6R)-6-dodecanoyloxymethyl-2-ethoxy-4,5-dihydroxy-tetrahydro-pyran-3-yl ester

Octadecanoic acid (2R,3R,4S,5S,6R)-2-ethoxy-4,5-dihydroxy-6-octadecanoyloxymethyl-tetrahydro-pyran-3-yl ester

ethyl α-D-glucopyranoside

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