beta-D-Glucopyranosiduronic acid, 2-(hydroxymethyl)-4-nitrophenyl, methyl ester, 2,3,4-triacetate

Base Information

• Chemical Name: beta-D-Glucopyranosiduronic acid, 2-(hydroxymethyl)-4-nitrophenyl, methyl ester, 2,3,4-triacetate
• CAS No.: 148579-84-4
• Molecular Formula: C₂₀H₂₃NO₁₃
• Molecular Weight: 485.402
• DSSTox Substance ID: DTXSID301117940
• Mol file: 148579-84-4.mol

Synonyms:SCHEMBL4268690;DTXSID301117940;148579-84-4;beta-D-Glucopyranosiduronic acid, 2-(hydroxymethyl)-4-nitrophenyl, methyl ester, 2,3,4-triacetate

Chemical Property of beta-D-Glucopyranosiduronic acid, 2-(hydroxymethyl)-4-nitrophenyl, methyl ester, 2,3,4-triacetate

Chemical Property:

• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 11
• Exact Mass: 485.11693979
• Heavy Atom Count: 34
• Complexity: 781

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OC1C(C(OC(C1OC(=O)C)OC2=C(C=C(C=C2)[N+](=O)[O-])CO)C(=O)OC)OC(=O)C
• Isomeric SMILES: CC(=O)O[C@H]1[C@@H]([C@H](O[C@H]([C@@H]1OC(=O)C)OC2=C(C=C(C=C2)[N+](=O)[O-])CO)C(=O)OC)OC(=O)C

Technology Process of beta-D-Glucopyranosiduronic acid, 2-(hydroxymethyl)-4-nitrophenyl, methyl ester, 2,3,4-triacetate

There total 3 articles about beta-D-Glucopyranosiduronic acid, 2-(hydroxymethyl)-4-nitrophenyl, 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: 75.0%

(2S,3R,4S,5S,6S)-2-(2-formyl-4-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (148579-83-3) → methyl {[2-(hydroxymethyl)-4-nitrophenyl] 2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate (148579-84-4)

Guidance literature:

With sodium tetrahydroborate; silica gel; In chloroform; isopropyl alcohol; at 0 ℃; for 0.75h;

DOI:10.1021/jm970589l

Reference yield:

5-Nitrosalicylaldehyde (97-51-8) → methyl {[2-(hydroxymethyl)-4-nitrophenyl] 2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate (148579-84-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / silver oxide / acetonitrile / 4 h / Ambient temperature

2: 75 percent / NaBH₄, silica gel HL₆₀ / CHCl₃; propan-2-ol / 0.75 h / 0 °C

With sodium tetrahydroborate; silica gel; silver(l) oxide; In chloroform; isopropyl alcohol; acetonitrile;

DOI:10.1021/jm970589l

Reference yield:

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → methyl {[2-(hydroxymethyl)-4-nitrophenyl] 2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate (148579-84-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / silver oxide / acetonitrile / 4 h / Ambient temperature

2: 75 percent / NaBH₄, silica gel HL₆₀ / CHCl₃; propan-2-ol / 0.75 h / 0 °C

With sodium tetrahydroborate; silica gel; silver(l) oxide; In chloroform; isopropyl alcohol; acetonitrile;

DOI:10.1021/jm970589l

upstream raw materials:

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

5-Nitrosalicylaldehyde

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

Downstream raw materials:

methyl {[2-(chloromethyl)-4-nitrophenyl] 2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate

(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[4-nitro-2-(4-nitro-phenoxycarbonyloxymethyl)-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester