N-[(2S,3R,4R,5S,6R)-2-Ethylsulfanyl-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

Base Information

• Chemical Name: N-[(2S,3R,4R,5S,6R)-2-Ethylsulfanyl-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS No.: 122331-70-8
• Molecular Formula: C10H19NO5S
• Molecular Weight: 265.32656
• DSSTox Substance ID: DTXSID10446935
• Mol file: 122331-70-8.mol

Synonyms:122331-70-8;N-[(2S,3R,4R,5S,6R)-2-Ethylsulfanyl-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide;N-((2S,3R,4R,5S,6R)-2-(Ethylthio)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide;FT-0668130;DTXSID10446935;N-[(2S,3R,4R,5S,6R)-2-(ETHYLSULFANYL)-4,5-DIHYDROXY-6-(HYDROXYMETHYL)OXAN-3-YL]ACETAMIDE

Chemical Property of N-[(2S,3R,4R,5S,6R)-2-Ethylsulfanyl-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

Chemical Property:

• Melting Point: 216-218°C
• Boiling Point: 566.9±50.0 °C(Predicted)
• PKA: 13.03±0.70(Predicted)
• PSA: 127.81000
• Density: 1.35±0.1 g/cm3(Predicted)
• LogP: -0.47650
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility.: DMSO, Methanol, Water
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 265.09839388
• Heavy Atom Count: 17
• Complexity: 265

Purity/Quality:

97% ^*data from raw suppliers

Ethyl 2-Acetamido-2-deoxy- ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCSC1C(C(C(C(O1)CO)O)O)NC(=O)C
• Isomeric SMILES: CCS[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)NC(=O)C
• Uses: It is used in the synthesis of modified carbohydrates with glycosidases: stereo- and regiospecific syntheses of lactosamine derivatives and related compounds. Ethyl 2-Acetamido-2-deoxy-β-D-thioglucopyranoside is used in the synthesis of modified carbohydrates with glycosidases: stereo- and regiospecific syntheses of lactosamine derivatives and related compounds.

Technology Process of N-[(2S,3R,4R,5S,6R)-2-Ethylsulfanyl-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

There total 3 articles about N-[(2S,3R,4R,5S,6R)-2-Ethylsulfanyl-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide 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: 100.0%

ethyl 2-acetamido-3,4,6-tetra-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside (4239-72-9) → Ethyl 1-sulfanyl-(2-acetamido-2-deoxy)-O-β-D-glucopyranoside (122331-70-8)

Guidance literature:

With sodium methylate; In methanol; for 3h; Ambient temperature;

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

Reference yield:

Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3) → Ethyl 1-sulfanyl-(2-acetamido-2-deoxy)-O-β-D-glucopyranoside (122331-70-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / ZnI₂ / 1,2-dichloro-ethane / 6 h / 50 °C

2: 100 percent / MeOH, NaOMe / 3 h / Ambient temperature

With methanol; sodium methylate; zinc(II) iodide; In 1,2-dichloro-ethane;

DOI:10.1016/0957-4166(96)00066-3

Reference yield:

2-acetamido-2-deoxy-D-glucose (7512-17-6,282727-46-2,478518-83-1,127959-06-2,78393-48-3) → Ethyl 1-sulfanyl-(2-acetamido-2-deoxy)-O-β-D-glucopyranoside (122331-70-8)

Guidance literature:

With hydrogenchloride; ethanethiol;

DOI:10.1039/jr9560002042

upstream raw materials:

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

2-acetamido-2-deoxy-D-glucose

Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester

Downstream raw materials:

Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-5-acetylamino-6-ethylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-4-yl ester

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