4-ForMyl-2-nitrophenyl β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate

Base Information

• Chemical Name: 4-ForMyl-2-nitrophenyl β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate
• CAS No.: 148579-93-5
• Molecular Formula: C₂₀H₂₁NO₁₃
• Molecular Weight: 483.386
• Mol file: 148579-93-5.mol

Synonyms:(2S,3R,4S,5S,6S)-2-(4-formyl-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property of 4-ForMyl-2-nitrophenyl β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate

Chemical Property:

• Melting Point: 180-182 °C
• Boiling Point: 582.6±50.0 °C(Predicted)
• Density: 1.44±0.1 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

4-Formyl-2-nitrophenylβ-D-GlucopyranosiduronicAcidMethylEster2,3,4-Triacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 4-Formyl-2-nitrophenyl β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate is used in the synthesis of Camptothecin-based anticancer therapy.

Technology Process of 4-ForMyl-2-nitrophenyl β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate

There total 10 articles about 4-ForMyl-2-nitrophenyl β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate 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: 98.0%

4-hydroxy-3-nitrobenzaldehyde (3011-34-5) + 2,3,4-Tri-O-acetyl-β-D-glucopyranuronic acid methylester (3082-95-9,72692-06-9,73464-50-3) → (2S,3R,4S,5S,6S)-2-(4-formyl-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (148579-93-5)

Guidance literature:

2,3,4-Tri-O-acetyl-β-D-glucopyranuronic acid methylester; With hydrogen bromide; acetic acid; In dichloromethane; at 0 - 20 ℃;

4-hydroxy-3-nitrobenzaldehyde; With silver(l) oxide; In acetonitrile; at 20 ℃; Darkness;

DOI:10.1002/anie.201916124

Reference yield: 96.0%

4-hydroxy-3-nitrobenzaldehyde (3011-34-5) + 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → (2S,3R,4S,5S,6S)-2-(4-formyl-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (148579-93-5)

Guidance literature:

With silver(l) oxide; In acetonitrile; for 4h;

DOI:10.1021/ja042162r

Reference yield: 90.0%

4-hydroxy-3-nitrobenzaldehyde (3011-34-5) + (3R,4S,5S,6S)-2-bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (57820-69-6) → (2S,3R,4S,5S,6S)-2-(4-formyl-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (148579-93-5)

Guidance literature:

With silver(l) oxide; In acetonitrile; at 20 ℃; Inert atmosphere;

upstream raw materials:

4-hydroxy-3-nitrobenzaldehyde

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

(3R,4S,5S,6S)-2-bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

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

Downstream raw materials:

(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-hydroxymethyl-2-nitro-phenoxy)-tetrahydro-pyran-2-carboxylic acid

methyl [2-nitro-4-(hydroxymethyl)phenyl-β-D-glucopyranosid]uronate

methyl [2-nitro-4-(O-tert-butyldiphenylsilylmethyl)phenyl-β-D-glucopyranosid]uronate

benzyl [(2-nitro-4-hydroxymethylphenyl)-2,3,4-tri-(O-tert-butyldimethylsilyl)-β-D-glucopyranosid]uronate

Refernces

• 1、 López Rivas, Paula,Müller, Christoph,Breunig, Christian,Hechler, Torsten,Pahl, Andreas,Arosio, Daniela,Belvisi, Laura,Pignataro, Luca,Dal Corso, Alberto,Gennari, Cesare. "β-Glucuronidase triggers extracellular MMAE release from an integrin-targeted conjugate". . p. 4705 - 4710. Retrieved 2019.
• 2、 Calatrava-Pérez, Elena,Elmes, Robert B. P.,Gunnlaugsson, Thorfinnur,Lynch, Dylan M.,Marchetti, Luke A.,McManus, Gavin J.,Scanlan, Eoin M.,Williams, D. Clive. "Real-Time Multi-Photon Tracking and Bioimaging of Glycosylated Theranostic Prodrugs upon Specific Enzyme Triggered Release". . . Retrieved 2021/12/09.
• 3、 -. "NEODEGRADER CONJUGATES". Paragraph 0525; 0527; 0554. . Retrieved 2021/10/11.