(2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(3-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triol

Base Information

• Chemical Name: (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(3-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triol
• CAS No.: 20838-44-2
• Molecular Formula: C12H15NO8
• Molecular Weight: 301.253
• European Community (EC) Number: 244-074-4
• DSSTox Substance ID: DTXSID30943077
• Nikkaji Number: J225.346A
• Wikidata: Q82920107
• Mol file: 20838-44-2.mol

Synonyms:20838-44-2;(2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(3-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triol;3-NITROPHENYL-BETA-D-GLUCOPYRANOSIDE;(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(3-nitrophenoxy)oxane-3,4,5-triol;3-Nitrophenyl beta-D-glucopyranoside;(2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(3-nitro-phenoxy)tetrahydro-2H-pyran-3,4,5-triol;3-Nitrophenyl b-D-glucopyranoside;EINECS 244-074-4;3-nitrophenyl hexopyranoside;SCHEMBL6843900;DTXSID30943077;AKOS016000620;A902262

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

Chemical Property:

• Melting Point: 171-172 °C
• Boiling Point: 573.5 °C at 760 mmHg
• PKA: 12.70±0.70(Predicted)
• Flash Point: 300.6 °C
• PSA: 145.20000
• Density: 1.599g/cm³
• LogP: -0.70330
• Storage Temp.: 2-8°C
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 301.07976644
• Heavy Atom Count: 21
• Complexity: 362

Purity/Quality:

99%, ^*data from raw suppliers

3-Nitrophenyl b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

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

There total 10 articles about (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(3-nitrophenoxy)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: 83.0%

Tetra-O-acetyl-m-nitrophenyl-α-D-galactopyranosid (52571-64-9) → meta-nitrophenyl-α-D-galactopyranoside (3150-25-2,20838-44-2,28541-80-2,56140-66-0,72200-66-9,52571-71-8)

Guidance literature:

With sodium hydroxide; In methanol;

DOI:10.1021/acs.bioconjchem.8b00902

Reference yield: 70.0%

→ m-nitrophenyl β-D-glucopyranoside (20838-44-2)

Guidance literature:

With methanol; In dichloromethane; for 0.333333h;

With sodium methylate; In dichloromethane;

Reference yield:

D-galactose pentaacetate (25878-60-8) → meta-nitrophenyl-α-D-galactopyranoside (3150-25-2,20838-44-2,28541-80-2,56140-66-0,72200-66-9,52571-71-8)

Guidance literature:

Multi-step reaction with 3 steps

1: benzylamine / N,N-dimethyl-formamide / 20 °C

2: trifluorormethanesulfonic acid / -35 - 20 °C

3: sodium hydroxide / methanol

With trifluorormethanesulfonic acid; benzylamine; sodium hydroxide; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/acs.bioconjchem.8b00902

upstream raw materials:

1-O-(3′-nitrophenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

meta-nitrophenol

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

α-D-glucopyranose peracetylate

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