1-Amino-1-deoxy-2,3,4-triacetate β-D-Glucopyranuronic Acid Methyl Ester

Base Information

• Chemical Name: 1-Amino-1-deoxy-2,3,4-triacetate β-D-Glucopyranuronic Acid Methyl Ester
• CAS No.: 14365-73-2
• Molecular Formula: C₁₃H₁₉NO₉
• Molecular Weight: 333.295
• Mol file: 14365-73-2.mol

Synonyms:1-Amino-1-deoxy-2,3,4-triacetate β-D-Glucopyranuronic Acid Methyl Ester

Chemical Property of 1-Amino-1-deoxy-2,3,4-triacetate β-D-Glucopyranuronic Acid Methyl Ester

Chemical Property:

Purity/Quality:

1-Amino-1-deoxy-2,3,4-triacetateβ-D-GlucopyranuronicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 1-Amino-1-deoxy-2,3,4-triacetate β-D-Glucopyranuronic Acid Methyl Ester is used in biological studies for the inhibitor identification of fibroblast growth factor (FGF-2) binding to heparin and endothelial cells.

Technology Process of 1-Amino-1-deoxy-2,3,4-triacetate β-D-Glucopyranuronic Acid Methyl Ester

There total 12 articles about 1-Amino-1-deoxy-2,3,4-triacetate β-D-Glucopyranuronic Acid Methyl 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: 80.0%

(S,S)-(-)-1,2-di(p-chlorophenyl)ethane-1,2-diol (325811-01-6) → 2,3,4-tri-O-acetyl-β-D-glucopyranosylamine uronic acid methyl ester (14365-73-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; at -15 ℃; for 3h;

DOI:10.1021/jo034336d

Reference yield:

2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-D-glucopyranuronic acid methyl ester (67776-38-9,163776-36-1) → 2,3,4-tri-O-acetyl-β-D-glucopyranosylamine uronic acid methyl ester (14365-73-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; at 0 ℃; for 2h; Irradiation;

DOI:10.1021/ja961068a

Reference yield:

methyl D-glucopyranuronate (82228-14-6) → 2,3,4-tri-O-acetyl-β-D-glucopyranosylamine uronic acid methyl ester (14365-73-2)

Guidance literature:

Multi-step reaction with 4 steps

1: HClO₄ / 4 - 20 °C

2: HBr / acetic acid / 5 °C

3: 92 percent / NaN₃; TBAHS / CH₂Cl₂; aq. NaHCO₃ / 2 h / 20 °C

4: H₂ / Pd/C / ethyl acetate / 20 °C

With sodium azide; perchloric acid; hydrogen bromide; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; palladium on activated charcoal; In dichloromethane; sodium hydrogencarbonate; acetic acid; ethyl acetate; 1: Acetylation / 2: Bromination / 3: azidation / 4: Reduction;

DOI:10.1016/S0008-6215(00)00228-7

upstream raw materials:

2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-D-glucopyranuronic acid methyl ester

(S,S)-(-)-1,2-di(p-chlorophenyl)ethane-1,2-diol

D-glucurono-6,3-lactone

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

Downstream raw materials:

(2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-[(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoylamino]-tetrahydro-pyran-2-carboxylic acid methyl ester

(2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(2-biphenyl-4-yl-acetylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester

7-methyl 1-deoxy-1-{[(2,4-dichlorophenoxy)acethyl]amino}-2,3,4-tri-O-acetyl-β-D-glucopyranuronate

(2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-[(2S,3R)-2-((S)-2-benzyloxycarbonylamino-6-tert-butoxycarbonylamino-hexanoylamino)-3-tert-butoxy-butyrylamino]-tetrahydro-pyran-2-carboxylic acid methyl ester

Refernces

• 1、 Fan, Zhanfang,Guo, Chun,Hou, Zhuang,Li, Chuanchao,Lin, Bin,Liu, Yang,Liu, Yichuang,Wang, Yitong,Zhang, Miao. "Design, synthesis and biological evaluation of carbohydrate-based sulphonamide derivatives as topical antiglaucoma agents through selective inhibition of carbonic anhydrase II". . p. 383 - 390. Retrieved 2019/12/30.
• 2、 -. "DIFFERENTIATION MODULATING AGENTS AND USES THEREFOR". Page/Page column 184. . Retrieved 2010/02/12.