N-((3R,4S,5S,6R)-2,3,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-YL)acetamide

Base Information

• Chemical Name: N-((3R,4S,5S,6R)-2,3,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-YL)acetamide
• CAS No.: 14086-88-5
• Molecular Formula: C8H15NO6
• Molecular Weight: 221.21
• Hs Code.: 29400090
• DSSTox Substance ID: DTXSID10930925
• Nikkaji Number: J1.345.260A
• Mol file: 14086-88-5.mol

Synonyms:SCHEMBL7643525;DTXSID10930925;AKOS015910580;3-(Acetylamino)-3-deoxy-D-glucopyranose;Glucopyranose,3-acetamido-3-deoxy-,d-(8ci);3-Deoxy-3-[(1-hydroxyethylidene)amino]hexopyranose;N-((3R,4S,5S,6R)-2,3,5-TRIHYDROXY-6-(HYDROXYMETHYL)TETRAHYDRO-2H-PYRAN-4-YL)ACETAMIDE

Chemical Property of N-((3R,4S,5S,6R)-2,3,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-YL)acetamide

Chemical Property:

• Appearance/Colour: White solid
• Melting Point: 204-205 °C
• Refractive Index: 1.576
• Boiling Point: 581.777 °C at 760 mmHg
• Flash Point: 305.648 °C
• PSA: 119.25000
• LogP: -2.68670
• Storage Temp.: 2-8°C
• Solubility.: Methanol (Slightly, Heated, Sonicated), Water (Slightly)
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 221.08993720
• Heavy Atom Count: 15
• Complexity: 235

Purity/Quality:

98%, ^*data from raw suppliers

3-Acetamido-3-deoxy-D-glucose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C(OC(C1O)O)CO)O
• Isomeric SMILES: CC(=O)N[C@H]1[C@@H]([C@H](OC([C@@H]1O)O)CO)O

Technology Process of N-((3R,4S,5S,6R)-2,3,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-YL)acetamide

There total 18 articles about N-((3R,4S,5S,6R)-2,3,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-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:

3-azido-3-deoxy-D-glucopyranose (104875-44-7) → 3-acetamido-3-deoxy-D-glucose (14086-88-5)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd(OH)2

2: methanol

With hydrogen; palladium dihydroxide; In methanol;

DOI:10.1021/ja00059a074

Reference yield:

3-amino-3-deoxy-D-glucopyranose (19309-98-9) + acetic anhydride (108-24-7) → 3-acetamido-3-deoxy-D-glucose (14086-88-5)

Guidance literature:

In methanol;

DOI:10.1021/ja00059a074

Reference yield:

1,2:5,6-di-O-isopropylidene-3-O-(methylsulphonyl)-α-D-allofuranose (14728-80-4) + acetic anhydride (108-24-7) → 3-acetamido-3-deoxy-D-glucose (14086-88-5)

Guidance literature:

Multistep reaction; (i) NaN₃, DMF, (ii) H₂, Pd-C, MeOH, (iii) /BRN= 385737/;

DOI:10.1002/cber.19681011120

upstream raw materials:

1,2:5,6-di-O-isopropylidene-3-O-(methylsulphonyl)-α-D-allofuranose

acetic anhydride

3-amino-3-deoxy-D-glucopyranose

3-azido-3-deoxy-D-glucopyranose

Downstream raw materials:

swainsonine

3-acetamido-2,4,5-tri-O-benzyl-3-deoxy-6-O-tosyl-D-mannose diethyl dithioacetal

swainsonine tribenzylate

(1S,2R,8R,8aR)-1,2,8-tris(benzyloxy)hexahydroindolizin-5(1H)-one

Refernces

• 1、 Meyer zu Reckendorf. "Synthesis of 3-amino-3-desoxy- and 3,6-diamino-3,6-didesoxy-D-glucose]". . p. 3802 - 3807. Retrieved 1968.
• 2、 Schmid, Walther,Zbiral, Erich. "A new Approach to 3-Acetylamino-3-desoxy-D-galactose". . p. 1253 - 1258. Retrieved 2007/10/02.