(Z)-N-[(4-hydroxyphenyl)methyl]ethoxycarbothioamide 4'-(tri-acetylrhamnoside)

Base Information

• Chemical Name: (Z)-N-[(4-hydroxyphenyl)methyl]ethoxycarbothioamide 4'-(tri-acetylrhamnoside)
• CAS No.: 147821-50-9
• Molecular Formula: C₂₂H₂₉NO₉S
• Molecular Weight: 483.54
• DSSTox Substance ID: DTXSID701110310
• Nikkaji Number: J650.613E
• Wikidata: Q76415445
• Mol file: 147821-50-9.mol

Synonyms:CHEBI:172709;DTXSID701110310;(Z)-N-[(4-hydroxyphenyl)methyl]ethoxycarbothioamide 4'-(tri-acetylrhamnoside);O-Ethyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamate;[(2S,3S,4R,5R,6S)-4,5-diacetyloxy-6-[4-[(ethoxycarbothioylamino)methyl]phenoxy]-2-methyloxan-3-yl] acetate;[4-(2-O,3-O,4-O-Triacetyl-alpha-L-rhamnopyranosyloxy)benzyl]thiocarbamic acid O-ethyl ester;147821-50-9;Carbamothioic acid, [[4-[(2,3,4-tri-O-acetyl-6-deoxy-alpha-L-mannopyranosyl)oxy]phenyl]methyl]-, O-ethyl ester

Chemical Property of (Z)-N-[(4-hydroxyphenyl)methyl]ethoxycarbothioamide 4'-(tri-acetylrhamnoside)

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 12
• Exact Mass: 483.15630268
• Heavy Atom Count: 33
• Complexity: 695

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=S)NCC1=CC=C(C=C1)OC2C(C(C(C(O2)C)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CCOC(=S)NCC1=CC=C(C=C1)O[C@H]2[C@@H]([C@@H]([C@H]([C@@H](O2)C)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of (Z)-N-[(4-hydroxyphenyl)methyl]ethoxycarbothioamide 4'-(tri-acetylrhamnoside)

There total 13 articles about (Z)-N-[(4-hydroxyphenyl)methyl]ethoxycarbothioamide 4'-(tri-acetylrhamnoside) 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: 17.0%

2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate (113893-72-4) + N-ethoxythiocarbonyl-4-hydroxy-benzylamine (198898-38-3) → N-ethoxythiocarbonyl-4-(2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyloxy)-benzylamine (147821-50-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -20 ℃; for 2h;

DOI:10.1016/S0008-6215(98)00223-7

Reference yield:

4-allyloxy-benzonitrile (33148-47-9) → N-ethoxythiocarbonyl-4-(2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyloxy)-benzylamine (147821-50-9)

Guidance literature:

Multi-step reaction with 6 steps

1: LiAlH₄ / diethyl ether / 24 h / Heating

2: Na₂CO₃ / acetone; H₂O / 2.5 h / Ambient temperature

3: 91 percent / HCOOH, PPh₃, Pd(OAc)2 / tetrahydrofuran / 4.5 h / Heating

4: 80 percent / NIS, MS, TfOH / CH₂Cl₂ / 2 h / -40 °C

5: H₂ / Pd / methanol / 6 h / Ambient temperature

6: dimethylformamide / 2.5 h / 80 °C

With palladium diacetate; N-iodo-succinimide; lithium aluminium tetrahydride; formic acid; trifluorormethanesulfonic acid; hydrogen; sodium carbonate; triphenylphosphine; palladium; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0008-6215(98)00223-7

Reference yield:

4-cyanophenol (767-00-0) → N-ethoxythiocarbonyl-4-(2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyloxy)-benzylamine (147821-50-9)

Guidance literature:

Multi-step reaction with 7 steps

1: NaH / dimethylformamide / 16 h / Ambient temperature

2: LiAlH₄ / diethyl ether / 24 h / Heating

3: Na₂CO₃ / acetone; H₂O / 2.5 h / Ambient temperature

4: 91 percent / HCOOH, PPh₃, Pd(OAc)2 / tetrahydrofuran / 4.5 h / Heating

5: 80 percent / NIS, MS, TfOH / CH₂Cl₂ / 2 h / -40 °C

6: H₂ / Pd / methanol / 6 h / Ambient temperature

7: dimethylformamide / 2.5 h / 80 °C

With palladium diacetate; N-iodo-succinimide; lithium aluminium tetrahydride; formic acid; trifluorormethanesulfonic acid; hydrogen; sodium hydride; sodium carbonate; triphenylphosphine; palladium; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0008-6215(98)00223-7

upstream raw materials:

acetic anhydride

niazimicin

niaziminin A + B

O-ethyl 4-[(α-L-rhamnosyloxy)benzyl]thiocarbamate

Downstream raw materials:

O-ethyl 4-[(α-L-rhamnosyloxy)benzyl]thiocarbamate