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

Base Information

• Chemical Name: tert-butyl (1R,2S,3S)-1-((R,Z)-4-hydroxy-7-iodohept-6-enyl)-2-((Z)-2-iodovinyl)-3-(methoxymethoxy)cyclohexylcarbamate
• CAS No.: 1321494-65-8
• Molecular Formula: C₂₂H₃₇I₂NO₅
• Molecular Weight: 649.348
• Mol file: 1321494-65-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about tert-butyl (1R,2S,3S)-1-((R,Z)-4-hydroxy-7-iodohept-6-enyl)-2-((Z)-2-iodovinyl)-3-(methoxymethoxy)cyclohexylcarbamate 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: 74.9%

tert-butyl (1R,2S,3S)-1-((R)-4-hydroxy-7-iodohept-6-ynyl)-2-(iodoethynyl)-3-(methoxymethoxy)cyclohexylcarbamate (1321495-04-8) → tert-butyl (1R,2S,3S)-1-((R,Z)-4-hydroxy-7-iodohept-6-enyl)-2-((Z)-2-iodovinyl)-3-(methoxymethoxy)cyclohexylcarbamate (1321494-65-8)

Guidance literature:

With 2-nitrobenzenesulfonyl hydrazide; triethylamine; In tetrahydrofuran; at 20 ℃; for 13h; Inert atmosphere;

DOI:10.1021/ol2018032

Reference yield:

tert-butyl (1R,2S,3S)-1-(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 (1321494-65-8) + tert-butyl (1R,2S,3S)-1-((S,Z)-4-hydroxy-7-iodohept-6-enyl)-2-((Z)-2-iodovinyl)-3-(methoxymethoxy)cyclohexylcarbamate

Guidance literature:

With 2-nitrobenzenesulfonyl hydrazide; triethylamine; In tetrahydrofuran; at 20 ℃; for 13h; Overall yield = 74.9 %; Overall yield = 430 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) → tert-butyl (1R,2S,3S)-1-((R,Z)-4-hydroxy-7-iodohept-6-enyl)-2-((Z)-2-iodovinyl)-3-(methoxymethoxy)cyclohexylcarbamate (1321494-65-8)

Guidance literature:

Multi-step reaction with 2 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

With 2-nitrobenzenesulfonyl hydrazide; iodine; triethylamine; potassium hydroxide; In tetrahydrofuran; methanol; water;

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

Downstream raw materials:

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

(R,Z)-7-((1S,2S,3S)-1-(tert-butoxycarbonylamino)-2-((Z)-2-iodovinyl)-3-(methoxymethoxy)cyclohexyl)-1-iodohept-1-en-4-yl methanesulfonate