(2R,3S,4R,5R,6S)-5-amino-6-[(2R,4R,5R)-5-amino-6-[(2R,3S,4R,5R,6R)-5-amino-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-2-(hydroxymethyl)oxane-3,4-diol

Base Information

• Chemical Name: (2R,3S,4R,5R,6S)-5-amino-6-[(2R,4R,5R)-5-amino-6-[(2R,3S,4R,5R,6R)-5-amino-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-2-(hydroxymethyl)oxane-3,4-diol
• CAS No.: 78341-33-0
• Molecular Formula: C₁₁H₂₁NO₆
• Molecular Weight: 263.291
• Metabolomics Workbench ID: 38506
• Mol file: 78341-33-0.mol

Synonyms:D-Glucosaminide;(2R,3S,4R,5R,6S)-5-amino-6-[(2R,4R,5R)-5-amino-6-[(2R,3S,4R,5R,6R)-5-amino-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-2-(hydroxymethyl)oxane-3,4-diol;n-2-yl]oxy-6-(hydroxymethyl)oxane-2,4-diol;4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxa;(2R,3R,4R,5S,6R)-3-amino-5-{[(3R,4R,6R)-3-amino-5-{[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-(hydroxymethyl)oxane-2,4-diol

Chemical Property of (2R,3S,4R,5R,6S)-5-amino-6-[(2R,4R,5R)-5-amino-6-[(2R,3S,4R,5R,6R)-5-amino-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-2-(hydroxymethyl)oxane-3,4-diol

Chemical Property:

• Boiling Point: 882.2oC at 760 mmHg
• Flash Point: 487.4oC
• PSA: 108.25000
• Density: 1.68g/cm3
• LogP: -1.25400
• XLogP3: -7.6
• Hydrogen Bond Donor Count: 11
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 7
• Exact Mass: 501.21698818
• Heavy Atom Count: 34
• Complexity: 652

Purity/Quality:

98% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(C(C(C(O1)OC2C(OC(C(C2O)N)OC3C(OC(C(C3O)N)O)CO)CO)N)O)O)O
• Isomeric SMILES: C([C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC2[C@H](OC([C@@H]([C@H]2O)N)O[C@@H]3[C@H](O[C@H]([C@@H]([C@H]3O)N)O)CO)CO)N)O)O)O
• Uses: ISO-PROPYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE can be used in the chemical synthesis of N-acetylglucosamine derivatives as glycosyl acceptors by the Mesorhizobium loti chitin oligosaccharide synthase NodC.

Technology Process of (2R,3S,4R,5R,6S)-5-amino-6-[(2R,4R,5R)-5-amino-6-[(2R,3S,4R,5R,6R)-5-amino-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-2-(hydroxymethyl)oxane-3,4-diol

There total 8 articles about (2R,3S,4R,5R,6S)-5-amino-6-[(2R,4R,5R)-5-amino-6-[(2R,3S,4R,5R,6R)-5-amino-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-2-(hydroxymethyl)oxane-3,4-diol 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: 95.0%

o-nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranoside (13264-92-1,152957-34-1) + isopropyl alcohol (67-63-0,8013-70-5) → isopropyl 2-acetamido-2-deoxy-β-D-glucopyranoside (78341-33-0)

Guidance literature:

With zinc(II) chloride; at 70 ℃; for 22h;

DOI:10.1016/S0008-6215(02)00470-6

Reference yield:

N-Acetyl-D-glucosamine (7512-17-6,72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4) + isopropyl alcohol (67-63-0,8013-70-5) → isopropyl 2-acetamido-2-deoxy-α-D-glucopyranoside (19124-40-4) + isopropyl 2-acetamido-2-deoxy-β-D-glucopyranoside (78341-33-0)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; at 20 ℃; Overall yield = 58 %;

DOI:10.1080/07328303.2017.1321116

Reference yield:

N'-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-p-toluenesulfono-hydrazide (1040191-33-0) + isopropyl alcohol (67-63-0,8013-70-5) → isopropyl 2-acetamido-2-deoxy-α-D-glucopyranoside (19124-40-4) + isopropyl 2-acetamido-2-deoxy-β-D-glucopyranoside (78341-33-0)

Guidance literature:

With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h; optical yield given as %de;

DOI:10.1021/ol801232f

upstream raw materials:

2-Acetylamino-2-desoxy-DL-glucopyranose

o-nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranoside

isopropyl alcohol

2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline

Refernces

• 1、 Gudmundsdottir, Anna V.,Nitz, Mark. "Protecting group free glycosidations using p-toluenesulfonohydrazide donors". supporting information; scheme or table. p. 3461 - 3463. Retrieved 2009/04/16.
• 2、 Pistia-Brueggeman, Gabriela,Hollingsworth, Rawle I.. "The use of the o-nitrophenyl group as a protecting/activating group for 2-acetamido-2-deoxyglucose". . p. 455 - 458. Retrieved 2007/10/03.