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

Base Information

• Chemical Name: N-[(2S,3R,4R,5S,6R)-2-(4-bromophenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS No.: 38229-80-0
• Molecular Formula: C₁₄H₁₈BrNO₆
• Molecular Weight: 376.204
• DSSTox Substance ID: DTXSID20474527
• Mol file: 38229-80-0.mol

Synonyms:38229-80-0;4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside;N-[(2S,3R,4R,5S,6R)-2-(4-bromophenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide;4'-bromophenyl 2-acetamido-2-deoxy-beta-d-glucopyranoside;DTXSID20474527;AKOS027380982;W-202568;4-Bromophenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside;Z1800406684

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

Chemical Property:

• Boiling Point: 642.1±55.0 °C(Predicted)
• PKA: 12.88±0.70(Predicted)
• Density: 1.65±0.1 g/cm3(Predicted)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 375.03175
• Heavy Atom Count: 22
• Complexity: 376

Purity/Quality:

98%Min ^*data from raw suppliers

4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1OC2=CC=C(C=C2)Br)CO)O)O
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC2=CC=C(C=C2)Br)CO)O)O

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

There total 4 articles about N-[(2S,3R,4R,5S,6R)-2-(4-bromophenoxy)-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:

p-bromophenyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (38229-74-2) → p-bromophenyl-N-acetyl-β-D-glucosaminide (38229-80-0)

Guidance literature:

With sodium methylate; In methanol; Ambient temperature;

Reference yield:

4-bromo-phenol (106-41-2) + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) → p-bromophenyl-N-acetyl-β-D-glucosaminide (38229-80-0)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutylammomium bromide; sodium hydroxide / dichloromethane; water / 1 h

2: sodium methylate / methanol / 1 h

With tetrabutylammomium bromide; sodium methylate; sodium hydroxide; In methanol; dichloromethane; water;

DOI:10.1039/d1ob00617g

Reference yield:

4-bromo-phenol (106-41-2) → p-bromophenyl-N-acetyl-β-D-glucosaminide (38229-80-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / tetrabutylammonium hydrogen sulfate, 1M NaOH / CH₂Cl₂ / 0.75 h / Ambient temperature

2: NaOMe / methanol / Ambient temperature

With sodium hydroxide; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; In methanol; dichloromethane;

upstream raw materials:

p-bromophenyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

4-bromo-phenol

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

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