(E)-2-{3'-[2'',5''-bis(methoxymethoxy)phenyl]prop-2-enylthio}-1,3-benzothiazole

Base Information

• Chemical Name: (E)-2-{3'-[2'',5''-bis(methoxymethoxy)phenyl]prop-2-enylthio}-1,3-benzothiazole
• CAS No.: 1580541-71-4
• Molecular Formula: C₂₀H₂₁NO₄S₂
• Molecular Weight: 403.523
• Mol file: 1580541-71-4.mol

Synonyms:(E)-2-{3'-[2'',5''-bis(methoxymethoxy)phenyl]prop-2-enylthio}-1,3-benzothiazole

Chemical Property of (E)-2-{3'-[2'',5''-bis(methoxymethoxy)phenyl]prop-2-enylthio}-1,3-benzothiazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-2-{3'-[2'',5''-bis(methoxymethoxy)phenyl]prop-2-enylthio}-1,3-benzothiazole

There total 4 articles about (E)-2-{3'-[2'',5''-bis(methoxymethoxy)phenyl]prop-2-enylthio}-1,3-benzothiazole 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: 89.0%

(E)-3-[2,5-bis(methoxymethoxy)phenyl]prop-2-en-1-ol (1580541-70-3) + 2-Mercaptobenzothiazole (149-30-4,118090-09-8) → (E)-2-{3'-[2'',5''-bis(methoxymethoxy)phenyl]prop-2-enylthio}-1,3-benzothiazole (1580541-71-4)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 0 - 20 ℃; for 10h;

DOI:10.1002/ejoc.201301269 DOI:10.1002/ejoc.201301269

Reference yield:

2,5-Dihydroxybenzaldehyde (1194-98-5) → (E)-2-{3'-[2'',5''-bis(methoxymethoxy)phenyl]prop-2-enylthio}-1,3-benzothiazole (1580541-71-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate / acetone / 10 h / 0 - 20 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

2.2: 1 h / 0 °C

3.1: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -78 - 0 °C

4.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 10 h / 0 - 20 °C

With sodium hydride; diisobutylaluminium hydride; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; acetone; toluene; mineral oil; 2.2: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1002/ejoc.201301269

Reference yield:

2,5-bis(methoxymethoxy)benzaldehyde (13709-07-4) → (E)-2-{3'-[2'',5''-bis(methoxymethoxy)phenyl]prop-2-enylthio}-1,3-benzothiazole (1580541-71-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

1.2: 1 h / 0 °C

2.1: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -78 - 0 °C

3.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 10 h / 0 - 20 °C

With sodium hydride; diisobutylaluminium hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; toluene; mineral oil; 1.2: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1002/ejoc.201301269

upstream raw materials:

2,5-Dihydroxybenzaldehyde

2,5-bis(methoxymethoxy)benzaldehyde

ethyl (E)-3-[2,5-bis(methoxymethoxy)phenyl]prop-2-enoate

(E)-3-[2,5-bis(methoxymethoxy)phenyl]prop-2-en-1-ol

Downstream raw materials:

(2'S,3'R)-2-{3'-[2'',5''-bis(methoxymethoxy)phenyl]-2',3'-dihydroxyprop-2-enylthio}-1,3-benzothiazole

(2'R,3'S)-2-{3'-[2'',5''-bis(methoxymethoxy)phenyl]-2',3'-dihydroxyprop-2-enylsulfonyl}-1,3-benzothiazole

(R)-1-[2',5'-bis(methoxymethoxy)phenyl]prop-2-en-1-ol

(S)-1-[2',5'-bis(methoxymethoxy)phenyl]prop-2-en-1-ol

Refernces

• 1、 Yajima, Arata,Urao, Shota,Katsuta, Ryo,Nukada, Tomoo. "Concise Syntheses and Biological Activities of Ganomycin i and Fornicin A". . p. 731 - 738. Retrieved 2015/10/05.