4,6-O-Ethylidene-D-glucopyranose

Base Information

• Chemical Name: 4,6-O-Ethylidene-D-glucopyranose
• CAS No.: 13224-99-2
• Molecular Formula: C8H14 O6
• Molecular Weight: 206.196
• Hs Code.: 29400090
• European Community (EC) Number: 236-198-2
• NSC Number: 89726
• DSSTox Substance ID: DTXSID30927594
• Mol file: 13224-99-2.mol

Synonyms:4,6-O-ethylidene glucose;ethylidene glucose

Chemical Property of 4,6-O-Ethylidene-D-glucopyranose

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 168-170 ºC
• Boiling Point: 386.571ºC at 760 mmHg
• PKA: 12.01±0.70(Predicted)
• Flash Point: 187.592ºC
• PSA: 88.38000
• Density: 1.447g/cm3
• LogP: -1.81320
• Solubility.: Ethanol, Water
• Water Solubility.: almost transparency
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 206.07903816
• Heavy Atom Count: 14
• Complexity: 210

Purity/Quality:

99% ^*data from raw suppliers

4,6-O-Ethylidene-α-D-glucopyranose ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

Useful:

• Canonical SMILES: CC1OCC2C(O1)C(C(C(O2)O)O)O
• Uses: 4,6-O-Ethylidene-D-glucose is an intermediate in synthesizing α-Etoposide (E933745), which is a cytotoxic agent (anticancer drug), which belongs to the drug type topoisomerase inhibitor. It is also an antineoplastic drug.

Technology Process of 4,6-O-Ethylidene-D-glucopyranose

There total 9 articles about 4,6-O-Ethylidene-D-glucopyranose 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: 93.0%

1,2,3-tri-O-acetyl-4,6-O-ethylidene-β-D-glucopyranose (105453-29-0) → (1’R)-(-)-4,6-O-ethylidene-D-glucose (13224-97-0,13224-98-1,13224-99-2,13225-00-8,13225-01-9,13225-02-0,18465-50-4,87068-63-1)

Guidance literature:

magnesium oxide; In methanol; for 0.5h; Ambient temperature;

DOI:10.1016/S0008-6215(00)90208-8

Reference yield: 92.0%

4,6-O-ethylidene-1,2,3-tri-O-acetyl-β-glucopyranose (27994-30-5) → 4,6-O-ethylidene-D-glucopyranose (18465-50-4,13224-97-0,13224-98-1,13224-99-2,13225-00-8,13225-01-9,13225-02-0,87068-63-1)

Guidance literature:

With methanol; potassium cyanide; for 4h; Ambient temperature;

DOI:10.1021/jo00355a026

Reference yield: 92.0%

D-Glucose (2280-44-6) + paracetaldehyde (123-63-7) → (1’R)-(-)-4,6-O-ethylidene-D-glucose (13224-97-0,13224-98-1,13224-99-2,13225-00-8,13225-01-9,13225-02-0,18465-50-4,87068-63-1)

Guidance literature:

With sulfuric acid; at 30 - 35 ℃; for 48h; ultrasonic irradiation;

DOI:10.3987/COM-06-S(K)28

upstream raw materials:

4,6-O-ethylidene-1,2,3-tri-O-acetyl-β-glucopyranose

1,2,3-tri-O-acetyl-4,6-O-ethylidene-β-D-glucopyranose

D-glucose

paracetaldehyde

Downstream raw materials:

methyl-alpha-D-glucopyranoside

2,4-O-Ethyliden-D-erythrit

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