Methanone, (4-nitrophenyl)(3-(beta-D-xylopyranosyloxy)phenyl)-

Base Information

• Chemical Name: Methanone, (4-nitrophenyl)(3-(beta-D-xylopyranosyloxy)phenyl)-
• CAS No.: 83355-06-0
• Molecular Formula: C₁₈H₁₇NO₈
• Molecular Weight: 375.335
• DSSTox Substance ID: DTXSID80232286
• Nikkaji Number: J571.368D
• Wikidata: Q76156788
• ChEMBL ID: CHEMBL171493
• Mol file: 83355-06-0.mol

Synonyms:(4-Nitrophenyl)(3-(beta-D-xylopyranosyloxy)phenyl)methanone;Methanone, (4-nitrophenyl)(3-(beta-D-xylopyranosyloxy)phenyl)-;83355-06-0;CHEMBL171493;DTXSID80232286;LS-91317;3-[4-Nitrobenzoyl]phenyl beta-D-xylopyranoside

Chemical Property of Methanone, (4-nitrophenyl)(3-(beta-D-xylopyranosyloxy)phenyl)-

Chemical Property:

• Vapor Pressure: 1.67E-17mmHg at 25°C
• Boiling Point: 644.7°Cat760mmHg
• Flash Point: 343.7°C
• Density: 1.514g/cm³
• XLogP3: 1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 375.09541650
• Heavy Atom Count: 27
• Complexity: 530

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C(O1)OC2=CC=CC(=C2)C(=O)C3=CC=C(C=C3)[N+](=O)[O-])O)O)O
• Isomeric SMILES: C1[C@H]([C@@H]([C@H]([C@@H](O1)OC2=CC=CC(=C2)C(=O)C3=CC=C(C=C3)[N+](=O)[O-])O)O)O

Technology Process of Methanone, (4-nitrophenyl)(3-(beta-D-xylopyranosyloxy)phenyl)-

There total 5 articles about Methanone, (4-nitrophenyl)(3-(beta-D-xylopyranosyloxy)phenyl)- 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:

Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-[3-(4-nitro-benzoyl)-phenoxy]-tetrahydro-pyran-3-yl ester (147029-63-8) → (4-Nitro-phenyl)-[3-((2S,3R,4S,5R)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-phenyl]-methanone (83355-06-0)

Guidance literature:

With sodium methylate; In methanol; for 2h; Ambient temperature;

DOI:10.1021/jm00059a015

Reference yield:

α-(3-methoxyphenyl)-4-morpholineacetonitrile (123567-57-7) → (4-Nitro-phenyl)-[3-((2S,3R,4S,5R)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-phenyl]-methanone (83355-06-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH, 3.) 70percent aq. AcOH

2: 70 percent / aq. HBr, AcOH / 4 h / Heating

3: 73 percent / Ag₂O / acetonitrile / 0.5 h / Ambient temperature

4: MeONa / methanol / 2 h / Ambient temperature

With hydrogen bromide; sodium methylate; sodium hydride; acetic acid; silver(l) oxide; In methanol; acetonitrile;

DOI:10.1021/jm00059a015

Reference yield:

3-methoxy-benzaldehyde (591-31-1) → (4-Nitro-phenyl)-[3-((2S,3R,4S,5R)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-phenyl]-methanone (83355-06-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 81 percent / TsOH / 3 h / Heating

2: 1.) NaH, 3.) 70percent aq. AcOH

3: 70 percent / aq. HBr, AcOH / 4 h / Heating

4: 73 percent / Ag₂O / acetonitrile / 0.5 h / Ambient temperature

5: MeONa / methanol / 2 h / Ambient temperature

With hydrogen bromide; sodium methylate; sodium hydride; toluene-4-sulfonic acid; acetic acid; silver(l) oxide; In methanol; acetonitrile;

DOI:10.1021/jm00059a015

upstream raw materials:

Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-[3-(4-nitro-benzoyl)-phenoxy]-tetrahydro-pyran-3-yl ester

α-(3-methoxyphenyl)-4-morpholineacetonitrile

3-methoxy-benzaldehyde

4'-nitro-3-hydroxybenzophenone