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

Base Information

• Chemical Name: (Z)-7-((1R,2R,3R,5S)-5-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-3-hydroxycyclopentyl)hept-5-enoic acid
• CAS No.: 1289580-06-8
• Molecular Formula: C₃₅H₆₂O₅Si₂
• Molecular Weight: 619.045
• Mol file: 1289580-06-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (Z)-7-((1R,2R,3R,5S)-5-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-3-hydroxycyclopentyl)hept-5-enoic acid 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:

(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)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-5-hydroxycyclopentyl)hept-5-enoic acid (1240483-23-1) + (Z)-7-((1R,2R,3R,5S)-5-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-3-hydroxycyclopentyl)hept-5-enoic acid (1289580-06-8)

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 ℃;

Reference yield:

(4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) → (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) + (Z)-7-((1R,2R,3R,5S)-5-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-3-hydroxycyclopentyl)hept-5-enoic acid (1289580-06-8)

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

With sodium hexamethyldisilazane; In tetrahydrofuran;

Reference yield:

(3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-4-((R)-3-((tert-butyldimethylsilyl)oxy)-5-phenylpentyl)hexahydro-2H-cyclopenta[b]furan-2-one (1240483-21-9) → (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) + (Z)-7-((1R,2R,3R,5S)-5-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-3-hydroxycyclopentyl)hept-5-enoic acid (1289580-06-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: diisobutylaluminium hydride / toluene / -40 °C / Inert atmosphere

1.2: 20 °C

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

2.2: 15 - 30 °C

With diisobutylaluminium hydride; In tetrahydrofuran; toluene;

upstream raw materials:

(4-carboxybutyl)triphenylphosphonium bromide

(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

(3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-4-((R)-3-((tert-butyldimethylsilyl)oxy)-5-phenylpentyl)hexahydro-2H-cyclopenta[b]furan-2-one