(R,Z)-7-((1S,2S,3S)-1-amino-3-hydroxy-2-((Z)-2-iodovinyl)cyclohexyl)-1-iodohept-1-en-4-yl methanesulfonate

Base Information

• Chemical Name: (R,Z)-7-((1S,2S,3S)-1-amino-3-hydroxy-2-((Z)-2-iodovinyl)cyclohexyl)-1-iodohept-1-en-4-yl methanesulfonate
• CAS No.: 1321494-66-9
• Molecular Formula: C₁₆H₂₇I₂NO₄S
• Molecular Weight: 583.27
• Mol file: 1321494-66-9.mol

Synonyms:(R,Z)-7-((1S,2S,3S)-1-amino-3-hydroxy-2-((Z)-2-iodovinyl)cyclohexyl)-1-iodohept-1-en-4-yl methanesulfonate

Chemical Property of (R,Z)-7-((1S,2S,3S)-1-amino-3-hydroxy-2-((Z)-2-iodovinyl)cyclohexyl)-1-iodohept-1-en-4-yl methanesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R,Z)-7-((1S,2S,3S)-1-amino-3-hydroxy-2-((Z)-2-iodovinyl)cyclohexyl)-1-iodohept-1-en-4-yl methanesulfonate

There total 4 articles about (R,Z)-7-((1S,2S,3S)-1-amino-3-hydroxy-2-((Z)-2-iodovinyl)cyclohexyl)-1-iodohept-1-en-4-yl methanesulfonate 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:

(Z)-7-((1S,2S,3S)-1-(tert-butoxycarbonylamino)-2-((Z)-2-iodovinyl)-3-(methoxymethoxy)cyclohexyl)-1-iodohept-1-en-4-yl methanesulfonate → (R,Z)-7-((1S,2S,3S)-1-amino-3-hydroxy-2-((Z)-2-iodovinyl)cyclohexyl)-1-iodohept-1-en-4-yl methanesulfonate (1321494-66-9) + (S,Z)-7-((1S,2S,3S)-1-amino-3-hydroxy-2-((Z)-2-iodovinyl)cyclohexyl)-1-iodohept-1-en-4-yl methanesulfonate

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 3h; Overall yield = 69.9 %; Overall yield = 23 mg; Inert atmosphere;

DOI:10.1021/ol5001632

Reference yield:

tert-butyl (1R,2S,3S)-2-ethynyl-1-((R)-4-hydroxyhept-6-ynyl)-3-(methoxymethoxy)-cyclohexylcarbamate (1321494-62-5) → (R,Z)-7-((1S,2S,3S)-1-amino-3-hydroxy-2-((Z)-2-iodovinyl)cyclohexyl)-1-iodohept-1-en-4-yl methanesulfonate (1321494-66-9)

Guidance literature:

Multi-step reaction with 4 steps

1: iodine; potassium hydroxide / methanol; water / 0.17 h / 0 - 20 °C / Inert atmosphere

2: 2-nitrobenzenesulfonyl hydrazide; triethylamine / tetrahydrofuran / 13 h / 20 °C / Inert atmosphere

3: triethylamine / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

4: boron trifluoride diethyl etherate / dichloromethane / 3 h / 20 °C / Inert atmosphere

With boron trifluoride diethyl etherate; 2-nitrobenzenesulfonyl hydrazide; iodine; triethylamine; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/ol2018032

Reference yield:

tert-butyl (1R,2S,3S)-1-((R)-4-hydroxy-7-iodohept-6-ynyl)-2-(iodoethynyl)-3-(methoxymethoxy)cyclohexylcarbamate (1321495-04-8) → (R,Z)-7-((1S,2S,3S)-1-amino-3-hydroxy-2-((Z)-2-iodovinyl)cyclohexyl)-1-iodohept-1-en-4-yl methanesulfonate (1321494-66-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 2-nitrobenzenesulfonyl hydrazide; triethylamine / tetrahydrofuran / 13 h / 20 °C / Inert atmosphere

2: triethylamine / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

3: boron trifluoride diethyl etherate / dichloromethane / 3 h / 20 °C / Inert atmosphere

With boron trifluoride diethyl etherate; 2-nitrobenzenesulfonyl hydrazide; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol2018032

upstream raw materials:

tert-butyl (1R,2S,3S)-2-ethynyl-1-((R)-4-hydroxyhept-6-ynyl)-3-(methoxymethoxy)-cyclohexylcarbamate

tert-butyl (1R,2S,3S)-1-((R)-4-hydroxy-7-iodohept-6-ynyl)-2-(iodoethynyl)-3-(methoxymethoxy)cyclohexylcarbamate

tert-butyl (1R,2S,3S)-1-((R,Z)-4-hydroxy-7-iodohept-6-enyl)-2-((Z)-2-iodovinyl)-3-(methoxymethoxy)cyclohexylcarbamate