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

Base Information

• Chemical Name: (2S,3R,4S,5S,6R)-2-(2-Chloro-4-nitrophenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• CAS No.: 120221-14-9
• Molecular Formula: C12H14 Cl N O8
• Molecular Weight: 335.698
• DSSTox Substance ID: DTXSID30595373
• Nikkaji Number: J2.233.285F
• Wikidata: Q82490373
• Mol file: 120221-14-9.mol

Synonyms:120221-14-9;(2S,3R,4S,5S,6R)-2-(2-Chloro-4-nitrophenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;2-Chloro-4-nitrophenyl beta-D-glucopyranoside;(2S,3R,4S,5S,6R)-2-(2-CHLORO-4-NITROPHENOXY)-6-(HYDROXYMETHYL)OXANE-3,4,5-TRIOL;2-Chloro-4-nitrophenyl-D-glucopyranoside;2-CHLORO-4-NITROPHENYL-BETA-D-GLUCO- PYRANOSIDE*;2-Chloro-4-nitrophenyl-beta-D-glucopyranoside;C12H14ClNO8;MFCD00037475;SCHEMBL3926021;DTXSID30595373;AKOS016000532;DS-5448;O10057;EN300-6732128;W-200938

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

Chemical Property:

• Boiling Point: 591.155°C at 760 mmHg (Cal.)
• PKA: 12.57±0.70(Predicted)
• Flash Point: 311.32°C (Cal.)
• PSA: 145.20000
• Density: 1.676g/cm3 (Cal.)
• LogP: -0.04990
• Storage Temp.: 2-8°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 335.0407941
• Heavy Atom Count: 22
• Complexity: 394

Purity/Quality:

98.0%min ^*data from raw suppliers

(2S,3R,4S,5S,6R)-2-(2-Chloro-4-nitrophenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1[N+](=O)[O-])Cl)OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1[N+](=O)[O-])Cl)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-(2-Chloro-4-nitrophenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

There total 9 articles about (2S,3R,4S,5S,6R)-2-(2-Chloro-4-nitrophenoxy)-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: 90.0%

(2-chloro-4-nitrophenyl) 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (35023-71-3,153823-58-6) → (2-chloro-4-nitrophenyl)-β-D-glucopyranoside (120221-14-9,119047-14-2)

Guidance literature:

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(2-chloro-4-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate; With sodium methylate; In methanol; at 20 ℃; for 18h;

In methanol;

DOI:10.1021/ol3023374

Reference yield:

D-glucose pentaacetate (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5) → (2-chloro-4-nitrophenyl)-β-D-glucopyranoside (120221-14-9,119047-14-2)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic anhydride; hydrogen bromide; acetic acid / 16 h / 20 °C

2: tetrabutylammomium bromide; sodium hydroxide / dichloromethane / 18 h / 20 °C

3: sodium methylate / methanol / 16 h / 20 °C

With tetrabutylammomium bromide; hydrogen bromide; sodium methylate; acetic anhydride; acetic acid; sodium hydroxide; In methanol; dichloromethane;

DOI:10.1002/anie.201603921

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (2-chloro-4-nitrophenyl)-β-D-glucopyranoside (120221-14-9,119047-14-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrabutylammomium bromide; sodium hydroxide / dichloromethane / 18 h / 20 °C

2.1: sodium methylate / methanol / 18 h / 20 °C

2.2: Amberlite IR-120 (H+ form)

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

DOI:10.1021/ol3023374

upstream raw materials:

2-chloro-4-nitrophenyl-β-maltopentoside

o-chloro-p-nitrophenyl β-maltotetraoside

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

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

Downstream raw materials:

D-Glucose

2-chloro-4-nitrophenol

(2-chloro-4-nitrophenyl) 6'-deoxy-6'-methoxyamino-β-D-glucopyranoside

(2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside