methyl 2-acetoxy-3,4-di-O-acetyl-D-arabino-hex-1-enopyranuronate

Base Information

• Chemical Name: methyl 2-acetoxy-3,4-di-O-acetyl-D-arabino-hex-1-enopyranuronate
• CAS No.: 62346-09-2
• Molecular Formula: C₁₃H₁₆O₉
• Molecular Weight: 316.265
• Mol file: 62346-09-2.mol

Synonyms:

Chemical Property of methyl 2-acetoxy-3,4-di-O-acetyl-D-arabino-hex-1-enopyranuronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-acetoxy-3,4-di-O-acetyl-D-arabino-hex-1-enopyranuronate

There total 2 articles about methyl 2-acetoxy-3,4-di-O-acetyl-D-arabino-hex-1-enopyranuronate 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:

(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester (7355-18-2) → methyl 2-acetoxy-3,4-di-O-acetyl-D-arabino-hex-1-enopyranuronate (62346-09-2) + 1-O-(4-Chlorphenyl)-2,3,4-tri-O-acetyl-β-D-glucopyran-methyl-uronat (82187-45-9)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen bromide; acetic acid / dichloromethane / Inert atmosphere

2: silver(l) oxide / quinoline / 24 h

With hydrogen bromide; acetic acid; silver(l) oxide; In quinoline; dichloromethane;

DOI:10.1039/c9ob01384a

Reference yield:

4-chloro-phenol (106-48-9,82344-39-6) + 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → methyl 2-acetoxy-3,4-di-O-acetyl-D-arabino-hex-1-enopyranuronate (62346-09-2) + 1-O-(4-Chlorphenyl)-2,3,4-tri-O-acetyl-β-D-glucopyran-methyl-uronat (82187-45-9)

Guidance literature:

With silver(l) oxide; In quinoline; for 24h;

DOI:10.1039/c9ob01384a

Reference yield:

methyl 2-acetoxy-3,4-di-O-acetyl-D-arabino-hex-1-enopyranuronate (62346-09-2) → 2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzyl-6-O-(methyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-β-D-mannopyranosyluronate)-β-D-glucopyranoside (152252-35-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 56 percent / NH₂OH*HCl, Py / 20 h / Ambient temperature

2: 1.) Py, 2.) NBS / 1.) 3 h, 2.) CCl4, hν, reflux, 30 min

3: 88 percent / silver aluminosilicate / CH₂Cl₂ / 2 h / Ambient temperature

4: 1.) BH₃-THF

With pyridine; N-Bromosuccinimide; borane-THF; silver aluminosilicate; hydroxylamine hydrochloride; In dichloromethane;

DOI:10.1246/bcsj.67.1130

upstream raw materials:

4-chloro-phenol

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Downstream raw materials:

2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzyl-6-O-(methyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-β-D-mannopyranosyluronate)-β-D-glucopyranoside