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
Hs Code.:
DSSTox Substance ID:DTXSID301117940

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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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%

: 148579-83-3
(2S,3R,4S,5S,6S)-2-(2-formyl-4-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

: 148579-84-4
methyl {[2-(hydroxymethyl)-4-nitrophenyl] 2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate

Guidance literature:: With sodium tetrahydroborate; silica gel; In chloroform; isopropyl alcohol; at 0 ℃; for 0.75h;
DOI:10.1021/jm970589l

Reference yield:

: 97-51-8
5-Nitrosalicylaldehyde

: 148579-84-4
methyl {[2-(hydroxymethyl)-4-nitrophenyl] 2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate

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:

: 21085-72-3
1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

: 148579-84-4
methyl {[2-(hydroxymethyl)-4-nitrophenyl] 2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate

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