2,3,4,6-Tetra-O-acetyl-|A-D-glucopyranosyl Ethylxanthate

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-acetyl-|A-D-glucopyranosyl Ethylxanthate
• CAS No.: 13639-54-8
• Molecular Formula: C₁₇H₂₄O₁₀S₂
• Molecular Weight: 452.504
• UNII: 6B7H7VSR0Q
• DSSTox Substance ID: DTXSID60159780
• Nikkaji Number: J789.854A
• Wikidata: Q72508731
• Mol file: 13639-54-8.mol

Synonyms:13639-54-8;NSC66060;6B7H7VSR0Q;NSC 66060;UNII-6B7H7VSR0Q;2,3,4,6-Tetra-O-acetyl-|A-D-glucopyranosyl Ethylxanthate;beta-D-Glucopyranose, 1-thio-, 2,3,4,6-tetraacetate 1-(O-ethyl carbonodithioate);beta-D-Glucopyranose, 1-thio-, 2,3,4,6-tetraacetate 1-(O-ethylcarbonodithioate);beta.-D-Glucopyranose, 1-thio-, 2,3,4,6-tetraacetate 1-(O-ethyl carbonodithioate);1-Thio-beta-D-glucopyranose 2,3,4,6-tetraacetate 1-(o-ethylcarbonodithioate);NSC-66060;SCHEMBL12611391;DTXSID60159780;GYORARISFGRNMU-LJIZCISZSA-N;AKOS016006378;2,3,4,6-Tetra-O-acetyl-?-D-glucopyranosyl Ethylxanthate;2,3,4,6-Tetra-O-acetyl- beta -D-glucopyranosyl Ethylxanthate;.beta.-D-Glucopyranose, 1-thio-, 2,3,4,6-tetraacetate 1-(O-ethylcarbonodithioate);1-(Ethoxycarbonothioylthio)-1-deoxy-beta-D-glucopyranose 2,3,4,6-tetraacetate;1-Thio-beta-D-glucopyranose-2,3,4,6-tetraacetate 1-(O-ethylcarbonodithioate);.BETA..-D-GLUCOPYRANOSE, 1-THIO-, 2,3,4,6-TETRAACETATE 1-(O-ETHYL CARBONODITHIOATE);[(2R,3R,4S,5R,6S)-3,4,5-triacetoxy-6-ethoxycarbothioylsulfanyl-tetrahydropyran-2-yl]methyl acetate;GLUCOPYRANOSE, 1-THIO-, 2,3,4,6-TETRAACETATE 1-(O-ETHYL DITHIOCARBONATE), .BETA.-D-

Chemical Property of 2,3,4,6-Tetra-O-acetyl-|A-D-glucopyranosyl Ethylxanthate

Chemical Property:

• Vapor Pressure: 1.1E-10mmHg at 25°C
• Melting Point: 88-890C
• Refractive Index: 1.535
• Boiling Point: 514.3 °C at 760 mmHg
• Flash Point: 264.8 °C
• PSA: 181.05000
• Density: 1.34
• LogP: 1.12410
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Ethyl Acetate, Methanol
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 13
• Exact Mass: 452.08108931
• Heavy Atom Count: 29
• Complexity: 638

Purity/Quality:

99% ^*data from raw suppliers

2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosylEthylxanthate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=S)SC1C(C(C(C(O1)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CCOC(=S)S[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Uses: 2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl Ethylxanthate (cas# 13639-54-8) is a compound useful in organic synthesis.

Technology Process of 2,3,4,6-Tetra-O-acetyl-|A-D-glucopyranosyl Ethylxanthate

There total 2 articles about 2,3,4,6-Tetra-O-acetyl-|A-D-glucopyranosyl Ethylxanthate 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: 86.0%

potassium ethyl xanthogenate (140-89-6) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 3,5-bis(acetyloxy)-2-[(acetyloxy)methyl]-6-[(ethoxycarbothioyl)sulfanyl] tetrahydro-2H-pyran-4-yl-acetate (4490-94-2,13639-54-8,29587-08-4,64879-61-4)

Guidance literature:

In acetonitrile; at 20 ℃; for 3h;

DOI:10.1021/ja004129k

Reference yield:

→ 3,5-bis(acetyloxy)-2-[(acetyloxy)methyl]-6-[(ethoxycarbothioyl)sulfanyl] tetrahydro-2H-pyran-4-yl-acetate (4490-94-2,13639-54-8,29587-08-4,64879-61-4)

Guidance literature:

2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl-bromid, Kalium-aethylxanthat/h.Aceton;

DOI:10.1248/cpb.11.1081

Reference yield: 17.0%

3,5-bis(acetyloxy)-2-[(acetyloxy)methyl]-6-[(ethoxycarbothioyl)sulfanyl] tetrahydro-2H-pyran-4-yl-acetate (4490-94-2,13639-54-8,29587-08-4,64879-61-4) → S-cyclohexyl O-ethyl carbonodithioate (54497-82-4) + 1,3,4,6-tetra-O-acetyl-2-deoxy-α-D-arabinohexopyranose (16750-06-4) + ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (32934-24-0,41670-79-5,52645-73-5,55722-49-1,79389-52-9,99031-86-4,125354-48-5,126187-25-5)

Guidance literature:

With dilauryl peroxide; cyclohexane; Heating;

DOI:10.1021/ja9619622

upstream raw materials:

potassium ethyl xanthogenate

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Downstream raw materials:

S-cyclohexyl O-ethyl carbonodithioate

1,3,4,6-tetra-O-acetyl-2-deoxy-α-D-arabinohexopyranose

ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside

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