METHYL-((4-NITROPHENYL)-2,3,4-TRI-O-ACETYL-BETA-D-GLUCOPYRANOSIDE)URONATE

Base Information

• Chemical Name: METHYL-((4-NITROPHENYL)-2,3,4-TRI-O-ACETYL-BETA-D-GLUCOPYRANOSIDE)URONATE
• CAS No.: 18472-49-6
• Molecular Formula: C19H21 N O12
• Molecular Weight: 455.375
• Hs Code.: 29400090
• Mol file: 18472-49-6.mol

Synonyms:Glucopyranosiduronicacid, p-nitrophenyl, methyl ester, 2,3,4-triacetate, b-D- (8CI); Glucopyranosiduronicacid, p-nitrophenyl, methyl ester, triacetate (6CI,7CI); Methyl p-nitrophenyl2,3,4-tri-O-acetyl-b-D-glucopyranosiduronate; Methyl p-nitrophenyl 2,3,4-tri-O-acetyl-b-D-glucouronate

Chemical Property of METHYL-((4-NITROPHENYL)-2,3,4-TRI-O-ACETYL-BETA-D-GLUCOPYRANOSIDE)URONATE

Chemical Property:

• Melting Point: 142-143°C
• PSA: 169.48000
• LogP: 1.18980
• Storage Temp.: ?20°C
• Solubility.: Dichloromethane, Ether, Ethyl Acetate, Methanol

Purity/Quality:

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

4-Nitrophenyl 2,3,4-tri-O-acetyl-b-D-glucuronide methyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-Nitrophenyl 2,3,4-tri-O-acetyl-β-D-glucuronic Acid, Methyl Ester (cas# 18472-49-6) is a compound useful in organic synthesis.

Technology Process of METHYL-((4-NITROPHENYL)-2,3,4-TRI-O-ACETYL-BETA-D-GLUCOPYRANOSIDE)URONATE

There total 16 articles about METHYL-((4-NITROPHENYL)-2,3,4-TRI-O-ACETYL-BETA-D-GLUCOPYRANOSIDE)URONATE 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: 88.1%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → methyl <4'-nitrophenyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid>uronate (18472-49-6)

Guidance literature:

4-nitro-phenol; With iodine; silver carbonate; In dichloromethane; for 0.166667h; Molecular sieve; Inert atmosphere;

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester; In dichloromethane; for 24h;

Reference yield: 85.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate (92420-89-8) → methyl <4'-nitrophenyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid>uronate (18472-49-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -10 ℃; for 1h;

DOI:10.1021/jo00199a046

Reference yield: 49.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate (3082-95-9,72692-06-9,73464-50-3) → (3aS,5S,6R,7S,7aS)-6,7-Diacetoxy-2-methyl-2-(4-nitro-phenoxy)-tetrahydro-[1,3]dioxolo[4,5-b]pyran-5-carboxylic acid methyl ester + (2S,3R,4S,5S,6S)-3,4,5-Triacetoxy-6-(4-nitro-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (18472-49-6,37797-58-3,40269-18-9,87392-27-6) + (2S,3R,4S,5S,6R)-3,4,5-Triacetoxy-6-(4-nitro-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (18472-49-6,37797-58-3,40269-18-9,87392-27-6)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 24h; Ambient temperature;

DOI:10.1016/0022-328X(90)85353-Z

upstream raw materials:

4-nitro-phenol

methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate

diazomethane

acetic anhydride

Downstream raw materials:

p-nitrophenyl-β-D-glucuronide

<4-(N-hydroxyacetamido)phenyl β-D-glucopyranosid>uronic acid

3,4,5-triacetoxy-6-{4-[3-(4-methoxy-benzenesulfonylamino)-pyridin-2-ylamino]-phenoxy}-tetrahydro-pyran-2-carboxylic acid methyl ester

3,4,5-triacetoxy-6-[4-(6-chloro-3-nitro-pyridin-2-ylamino)-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

Refernces

• 1、 -. "Preparation method of substituted benzyl or substituted phenyl beta-D-hexuronic acid glucoside". Paragraph 0062; 0076; 0077; 0078. . Retrieved 2018/10/19.
• 2、 Jongkees, Seino A. K.,Withers, Stephen G.. "Glycoside cleavage by a new mechanism in unsaturated glucuronyl hydrolases". supporting information; experimental part. p. 19334 - 19337. Retrieved 2012/01/31.