(2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-β-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime

Base Information

• Chemical Name: (2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-β-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime
• CAS No.: 1397274-89-3
• Molecular Formula: C₃₄H₂₇ClN₂O₁₁
• Molecular Weight: 675.048
• Mol file: 1397274-89-3.mol

Synonyms:(2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-β-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime

Chemical Property of (2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-β-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-β-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime

There total 8 articles about (2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-β-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime 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: 84.0%

C33H24ClNO11 + N-methoxylamine hydrochloride (593-56-6) → (2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-β-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime (1397274-89-3)

Guidance literature:

With pyridine; at 20 ℃; for 2h;

DOI:10.1021/ol3023374

Reference yield:

(2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-β-D-glucopyranoside (1397274-88-2) → (2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-β-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime (1397274-89-3)

Guidance literature:

Multi-step reaction with 2 steps

1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

2: pyridine / 2 h / 20 °C

With pyridine; Dess-Martin periodane; In dichloromethane;

DOI:10.1021/ol3023374

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-β-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime (1397274-89-3)

Guidance literature:

Multi-step reaction with 7 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)

3.1: 1H-imidazole / N,N-dimethyl-formamide / 48 h / 20 °C

4.1: pyridine / 16 h / 20 °C

5.1: acetyl chloride; methanol / diethyl ether / 40 h / 20 °C

6.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

7.1: pyridine / 2 h / 20 °C

With pyridine; 1H-imidazole; methanol; tetrabutylammomium bromide; sodium methylate; Dess-Martin periodane; acetyl chloride; sodium hydroxide; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol3023374

upstream raw materials:

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

(2-chloro-4-nitrophenyl)-β-D-glucopyranoside

(2-chloro-4-nitrophenyl) 6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside

Downstream raw materials:

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

(2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-β-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime

Refernces