2,3,4-Tri-O-benzoyl-alpha-D-glucopyranuronic acid methyl ester trichloroacetimidate

Base Information

• Chemical Name: 2,3,4-Tri-O-benzoyl-alpha-D-glucopyranuronic acid methyl ester trichloroacetimidate
• CAS No.: 169557-99-7
• Molecular Formula: C30H24 Cl3 N O10
• Molecular Weight: 664.88
• Mol file: 169557-99-7.mol

Synonyms:2,3,4-Tri-O-benzoyl-a-D-glucuronide methyl ester trichloroacetimidate;Methyl2,3,4-tri-O-benzoyl-a-D-glucopyranuronosyltrichloroacetimidate;2,3,4,5;

Chemical Property of 2,3,4-Tri-O-benzoyl-alpha-D-glucopyranuronic acid methyl ester trichloroacetimidate

Chemical Property:

• Melting Point: 136-139°C
• Boiling Point: 685.1±65.0 °C(Predicted)
• PKA: 1.39±0.70(Predicted)
• PSA: 147.51000
• Density: 1.45±0.1 g/cm3(Predicted)
• LogP: 5.02490
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,3,4-Tri-O-benzoyl-a-D-glucuronide methyl ester trichloroacetimidate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2,3,4-Tri-O-benzoyl-α-D-glucuronic Acid Methyl Ester, Trichloroacetimidate (cas# 169557-99-7) is a compound useful in organic synthesis.

Technology Process of 2,3,4-Tri-O-benzoyl-alpha-D-glucopyranuronic acid methyl ester trichloroacetimidate

There total 22 articles about 2,3,4-Tri-O-benzoyl-alpha-D-glucopyranuronic acid methyl ester trichloroacetimidate 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: 89.2%

methyl 2,3,4-tri-O-benzoyl-D-glucopyranuronate + trichloroacetonitrile (545-06-2) → 2,3,4-tri-O-benzoyl-1-deoxy-1-(2,2,2-trichloro-1-iminoethoxy)-α-D-glucopyranuronate, methyl ester (169557-99-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; for 3h;

Reference yield: 84.0%

trichloroacetonitrile (545-06-2) + methyl (2,3,4-tri-O-benzoyl-α-D-glucopyranosyluronate) (548477-88-9) → 2,3,4-tri-O-benzoyl-1-deoxy-1-(2,2,2-trichloro-1-iminoethoxy)-α-D-glucopyranuronate, methyl ester (169557-99-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2016.12.055

Reference yield:

benzoyl chloride (98-88-4) → 2,3,4-tri-O-benzoyl-1-deoxy-1-(2,2,2-trichloro-1-iminoethoxy)-α-D-glucopyranuronate, methyl ester (169557-99-7)

Guidance literature:

Multi-step reaction with 6 steps

1: DMAP, pyridine

2: HF, pyridine

3: Jones reagent

5: H₂ / Pd/C

6: DBU / 0.33 h / 0 °C

With pyridine; dmap; jones reagent; hydrogen fluoride; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal;

DOI:10.1021/ja9832358

upstream raw materials:

trichloroacetonitrile

methyl (2,3,4-tri-O-benzoyl-α-D-glucopyranosyluronate)

benzoyl chloride

benzyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside

Downstream raw materials:

4-methoxyphenyl (methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranuronate)-(1→3)-4-O-benzoyl-2,6-di-O-benzyl-β-D-galactopyranoside

4-methoxyphenyl O-(methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(2-O-benzoyl-4,6-O-di-tert-butylsilylene-β-D-galactopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside

Refernces

• 1、 Hou, Zhuang,Liu, Yang,Zhang, Xin-xin,Chang, Xiao-wei,Cheng, Mao-sheng,Guo, Chun. "Synthesis of glucuronic acid derivatives via the efficient and selective removal of a C6 methyl group". supporting information. p. 423 - 426. Retrieved 2017/01/10.
• 2、 Allen, John G.,Fraser-Reid, Bert. "n-Pentenyl glycosyl orthoesters as versatile intermediates in oligosaccharide synthesis. The proteoglycan linkage region". . p. 468 - 469. Retrieved 2007/10/03.