(2S,3R,4S,5S,6R)-2-(4-Aminophenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Base Information

• Chemical Name: (2S,3R,4S,5S,6R)-2-(4-Aminophenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• CAS No.: 20818-25-1
• Molecular Formula: C12H17NO6
• Molecular Weight: 271.27
• Hs Code.: 29400090
• European Community (EC) Number: 846-348-4
• UNII: 6R09NV3HOW
• DSSTox Substance ID: DTXSID60943065
• Nikkaji Number: J669.216H
• Wikidata: Q27094170
• Mol file: 20818-25-1.mol

Synonyms:4-aminophenyl glucoside;4-aminophenyl glucoside, (alpha-D)-isomer;4-aminophenyl-beta-D-glucopyranoside;p-aminophenyl-beta-D-glucoside;PAPB-DG

Chemical Property of (2S,3R,4S,5S,6R)-2-(4-Aminophenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Chemical Property:

• Vapor Pressure: 3.43E-13mmHg at 25°C
• Melting Point: 157-160℃
• Refractive Index: 1.662
• Boiling Point: 555.9 °C at 760 mmHg
• PKA: 12.93±0.70(Predicted)
• Flash Point: 290 °C
• PSA: 125.40000
• Density: 1.517 g/cm³
• LogP: -0.97130
• Storage Temp.: −20°C
• XLogP3: -1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 271.10558726
• Heavy Atom Count: 19
• Complexity: 283

Purity/Quality:

98%, ^*data from raw suppliers

4-Aminophenyl b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1N)OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O

Technology Process of (2S,3R,4S,5S,6R)-2-(4-Aminophenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

There total 11 articles about (2S,3R,4S,5S,6R)-2-(4-Aminophenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 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%

4-nitrophenyl-β-D-glucoside (2492-87-7) → 4-aminophenyl β-D-glucopyranoside (20818-25-1)

Guidance literature:

With 10% palladium on carbon; hydrogen; In methanol;

DOI:10.1016/j.bmcl.2010.03.003

Reference yield: 92.3%

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-aminophenoxy)-tetrahydro-2H-pyran-3,4,5-triyl triacetate (42011-36-9) → 4-aminophenyl β-D-glucopyranoside (20818-25-1)

Guidance literature:

With potassium carbonate; In methanol; Ambient temperature;

DOI:10.1248/cpb.38.13

Reference yield: 72.0%

4-amino-phenol (123-30-8) + 1-deoxy-1-fluoro-α-D-glucose (2106-10-7) → 4-aminophenyl β-D-glucopyranoside (20818-25-1)

Guidance literature:

With calcium hydroxide; In water; at 20 ℃; for 1h;

DOI:10.1038/s41557-018-0041-8

upstream raw materials:

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-aminophenoxy)-tetrahydro-2H-pyran-3,4,5-triyl triacetate

4-nitrophenyl-β-D-glucoside

p-nitrophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyde

4-nitro-phenol

Downstream raw materials:

C₄₄H₄₀N₂O₁₀

C₅₂H₅₆N₂O₁₀

C₄₈H₄₈N₂O₁₀

C₂₂H₂₇ClN₂O₁₀

Refernces

• 1、 Jung, Jong Hwa,John, George,Yoshida, Kaname,Shimizu, Toshimi. "Self-assembling structures of long-chain phenyl glucoside influenced by the introduction of double bonds". . p. 10674 - 10675. Retrieved 2002.
• 2、 Jung, Jong Hwa,Shimizu, Toshimi. "Direct sol-gel replication of the self-assembled nanostructure modified with H-bond functionalities". . p. 1246 - 1247. Retrieved 2002.
• 3、 Hoshing, Raghuraj,Saladino, Michael,Kuhn, Helene,Caianiello, David,Lusi, Robert F.,Basu, Amit. "An Improved Protocol for the Synthesis and Purification of Yariv Reagents". . p. 16236 - 16242. Retrieved 2020/11/20.