(Z)-isopropyl 7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-5-hydroxycyclopentyl)hept-5-enoate

Base Information

• Chemical Name: (Z)-isopropyl 7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-5-hydroxycyclopentyl)hept-5-enoate
• CAS No.: 474944-22-4
• Molecular Formula: C₃₈H₆₈O₅Si₂
• Molecular Weight: 661.126
• Mol file: 474944-22-4.mol

Synonyms:(Z)-isopropyl 7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-5-hydroxycyclopentyl)hept-5-enoate

Chemical Property of (Z)-isopropyl 7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-5-hydroxycyclopentyl)hept-5-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-isopropyl 7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-5-hydroxycyclopentyl)hept-5-enoate

There total 5 articles about (Z)-isopropyl 7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-5-hydroxycyclopentyl)hept-5-enoate 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-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-5-hydroxycyclopentyl)hept-5-enoic acid (1240483-23-1) + isopropyl bromide (75-26-3) → (Z)-isopropyl 7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-5-hydroxycyclopentyl)hept-5-enoate (474944-22-4)

Guidance literature:

(Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-5-hydroxycyclopentyl)hept-5-enoic acid; With caesium carbonate; In N,N-dimethyl-formamide; at 25 - 30 ℃; for 0.25h;

isopropyl bromide; In N,N-dimethyl-formamide; at 25 - 45 ℃;

Reference yield:

2-iodo-propane (75-30-9) + (3aR,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)hexahydro-2H-cyclopenta[b]furan-2-ol (1240483-22-0) + 4-carboxybutyliden triphenylphosphorane sodium (41723-91-5) → (Z)-isopropyl 7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-5-hydroxycyclopentyl)hept-5-enoate (474944-22-4) + (Z)-isopropyl 7-((1R,2R,3R,5S)-5-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-3-hydroxycyclopentyl)hept-5-enoate

Guidance literature:

(3aR,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)hexahydro-2H-cyclopenta[b]furan-2-ol; 4-carboxybutyliden triphenylphosphorane sodium; In tetrahydrofuran; at -15 - -5 ℃; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; n-heptane; ethyl acetate; at 15 - 30 ℃;

2-iodo-propane; With potassium carbonate; In N,N-dimethyl-formamide; at 40 ℃; Inert atmosphere;

Reference yield:

(4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) → (Z)-isopropyl 7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-5-hydroxycyclopentyl)hept-5-enoate (474944-22-4) + (Z)-isopropyl 7-((1R,2R,3R,5S)-5-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-3-hydroxycyclopentyl)hept-5-enoate

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 20 °C / Inert atmosphere

2.1: tetrahydrofuran / -15 - -5 °C / Inert atmosphere

2.2: 15 - 30 °C

2.3: 40 °C / Inert atmosphere

With sodium hexamethyldisilazane; In tetrahydrofuran;

upstream raw materials:

(Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-5-hydroxycyclopentyl)hept-5-enoic acid

isopropyl bromide

(4-carboxybutyl)triphenylphosphonium bromide

2-iodo-propane

Downstream raw materials:

latanoprost