2,3,4-Tri-O-benzyl-D-glucuronic acid benzyl ester

Base Information

• Chemical Name: 2,3,4-Tri-O-benzyl-D-glucuronic acid benzyl ester
• CAS No.: 4539-78-0
• Molecular Formula: C34H34O7
• Molecular Weight: 554.64
• Hs Code.: 2940000080
• Mol file: 4539-78-0.mol

Synonyms:2,3,4-Tri-O-benzyl-D-glucuronic acid benzyl ester;Benzyl 2,3,4-tri-O-benzyl-D-glucopyranosyluronate min. 98%;2,3,4-Tri-O-benzylglucopyranuronic acid benzyl ester

Chemical Property of 2,3,4-Tri-O-benzyl-D-glucuronic acid benzyl ester

Chemical Property:

• PSA: 83.45000
• LogP: 5.20320

Purity/Quality:

99% ^*data from raw suppliers

Benzyl2,3,4-Tri-O-benzyl-D-glucuronate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,3,4-Tri-O-benzyl-D-glucuronic acid benzyl ester

There total 9 articles about 2,3,4-Tri-O-benzyl-D-glucuronic acid benzyl ester 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%

(2S,3S,4S,5R,6R)-6-Allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid benzyl ester (185380-13-6) → 2,3,4-tri-O-benzyl-D-glucopyranosideuronic acid benzyl ester (4539-78-0)

Guidance literature:

With sodium acetate; acetic acid; palladium dichloride; at 60 ℃; for 1.5h;

DOI:10.1246/bcsj.69.3247

Reference yield:

methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate (3082-96-0,5432-32-6,7355-18-2,19231-41-5,30628-06-9,30628-07-0,40268-90-4,40268-95-9,40269-24-7,104195-05-3,108032-41-3) → 2,3,4-tri-O-benzyl-D-glucopyranosideuronic acid benzyl ester (4539-78-0)

Guidance literature:

Multi-step reaction with 6 steps

1: aq. AcBr / CHCl₃

2: Ag₂CO₃ / Ambient temperature

3: 84 percent / NaOMe / methanol / 1.5 h / Ambient temperature

4: 60 percent / NaH / dimethylsulfoxide / 0.42 h / 15 - 20 °C

5: 1.) aq. NaOH / 1.) 1,2-dimethoxyethane, 25 deg C, overnight, 2.) DMSO, 25 deg C, 2.5 h

6: 83 percent / NaOAc, aq. AcOH, PdCl₂ / 1.5 h / 60 °C

With sodium hydroxide; Acetyl bromide; sodium methylate; sodium acetate; sodium hydride; acetic acid; silver carbonate; palladium dichloride; In methanol; chloroform; dimethyl sulfoxide;

DOI:10.1246/bcsj.69.3247

Reference yield:

(3R,4S,5S,6S)-2-bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (57820-69-6) → 2,3,4-tri-O-benzyl-D-glucopyranosideuronic acid benzyl ester (4539-78-0)

Guidance literature:

Multi-step reaction with 5 steps

1: Ag₂CO₃ / Ambient temperature

2: 84 percent / NaOMe / methanol / 1.5 h / Ambient temperature

3: 60 percent / NaH / dimethylsulfoxide / 0.42 h / 15 - 20 °C

4: 1.) aq. NaOH / 1.) 1,2-dimethoxyethane, 25 deg C, overnight, 2.) DMSO, 25 deg C, 2.5 h

5: 83 percent / NaOAc, aq. AcOH, PdCl₂ / 1.5 h / 60 °C

With sodium hydroxide; sodium methylate; sodium acetate; sodium hydride; acetic acid; silver carbonate; palladium dichloride; In methanol; dimethyl sulfoxide;

DOI:10.1246/bcsj.69.3247

upstream raw materials:

(2S,3S,4S,5R,6S)-6-Allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid benzyl ester

(2S,3S,4S,5R,6R)-6-Acetoxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid benzyl ester

(2S,3S,4S,5R,6R)-6-Allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid benzyl ester

methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate

Downstream raw materials:

benzyl 2,3,4-tri-O-benzyl-1-O-(1-benzyl N-benzyloxycarbonyl-L-glutam-5-oyl)-D-glucopyranuronate

benzyl 2,3,4-tri-O-benzyl-1-O-(1-benzyl N-benzyloxycarbonyl-L-glutam-5-oyl)-D-glucopyranuronate

benzyl 2,3,4-tri-O-benzyl-1-O--D-glucopyranuronate

benzyl 2,3,4-tri-O-benzyl-1-O--D-glucopyranuronate

Refernces

• 1、 Kaspersen, Frans M.,Boeckel, Constant A. A. van,Delbressine, Leon P. C.,Koten, Annemiek,Jacobs, Peter L.,Funke, Carel W.. "Synthesis of a novel carbamate-glucuronide". . p. C11 - C13. Retrieved 2007/10/02.