(5-Acetamido-3,4-diacetyloxy-6-ethylsulfanyloxan-2-yl)methyl acetate

Base Information

• Chemical Name: (5-Acetamido-3,4-diacetyloxy-6-ethylsulfanyloxan-2-yl)methyl acetate
• CAS No.: 49810-41-5
• Molecular Formula: C₁₆H₂₅NO₈S
• Molecular Weight: 391.442
• DSSTox Substance ID: DTXSID70402193
• Mol file: 49810-41-5.mol

Synonyms:49810-41-5;(5-acetamido-3,4-diacetyloxy-6-ethylsulfanyloxan-2-yl)methyl acetate;Ethyl 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-beta-D-galactopyranoside;Ethyl 2-acetamido-3,4,6-tri-o-acetyl-2-deoxy-beta-d-thioglucopyranoside;MFCD31814466;DTXSID70402193;SY249900;FT-0659064;FT-0668406;A827860;Ethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thiohexopyranoside

Chemical Property of (5-Acetamido-3,4-diacetyloxy-6-ethylsulfanyloxan-2-yl)methyl acetate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.512
• Boiling Point: 547.858oC at 760 mmHg
• Flash Point: 285.134oC
• PSA: 142.53000
• Density: 1.261g/cm3
• LogP: 0.78650
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 10
• Exact Mass: 391.13008793
• Heavy Atom Count: 26
• Complexity: 540

Purity/Quality:

98% ^*data from raw suppliers

Ethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-a-D-thioglucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCSC1C(C(C(C(O1)COC(=O)C)OC(=O)C)OC(=O)C)NC(=O)C
• Uses: Ethyl 3,4,6-Tri-O-acetyl-2-acetamido-2-deoxy-a-D- thioglucopyranoside is a kind of useful reagent for the preparation of GlcNAc glycosides.

Technology Process of (5-Acetamido-3,4-diacetyloxy-6-ethylsulfanyloxan-2-yl)methyl acetate

There total 3 articles about (5-Acetamido-3,4-diacetyloxy-6-ethylsulfanyloxan-2-yl)methyl acetate 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: 83.0%

(ethylthio)trimethylsilane (5573-62-6) + (3R,4R,5R,6R)-3-acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate (76375-60-5) → ethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-galactopyranoside (4239-72-9,10277-32-4,49810-41-5,144218-98-4)

Guidance literature:

With zinc(II) iodide; In dichloromethane; at 50 ℃; for 8h;

DOI:10.1016/S0957-4166(00)86294-1

Reference yield:

D-galactosamine (90-76-6,90-77-7,530-23-4,579-32-8,579-33-9,643-68-5,2596-19-2,6490-68-2,6490-70-6,6490-72-8,6490-73-9,6490-74-0,14196-84-0,14196-86-2,14257-69-3,58381-21-8) + acetic anhydride (108-24-7) + ethanethiol (75-08-1) → 2-acetamido-3,4,5,6-tetra-O-acetyl-2-deoxy-D-galactose diethyl dithioacetal (112578-78-6) + ethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-galactopyranoside (4239-72-9,10277-32-4,49810-41-5,144218-98-4)

Guidance literature:

With pyridine; hydrogenchloride; Yield given. Multistep reaction. Yields of byproduct given; 1) r. t., 2 d, 2) r. t., overnight;

DOI:10.1016/S0008-6215(00)91006-1

Reference yield:

→ ethyl-(tri-O-acetyl-2-acetylamino-1-thio-2-deoxy-α-D-glucopyranoside) (49810-41-5)

Guidance literature:

With pyridine; acetic anhydride;

DOI:10.1039/jr9560002042

upstream raw materials:

D-galactosamine

acetic anhydride

ethanethiol

(ethylthio)trimethylsilane

Refernces

• 1、 Adelhorst, Kim,Whitesides, George M.. "Synthesis of 2-amino-1,2-dideoxy-D-galacitol hydrochloride and 5-amino-1,4-anhydro-5,6-dideoxy-L-galacitol hydrochloride". . p. 183 - 188. Retrieved 2007/10/02.