(3aR,4R,5R,6aS)-4-[(3R)-(tert-butyldimethylsilyl)oxy-5-phenylpentyl]perhydrocyclopenta[b]furan-2,5-diol

Base Information

Chemical Name:(3aR,4R,5R,6aS)-4-[(3R)-(tert-butyldimethylsilyl)oxy-5-phenylpentyl]perhydrocyclopenta[b]furan-2,5-diol
CAS No.:1393740-68-5
Molecular Formula:C₃₁H₅₁NO₄Si
Molecular Weight:529.836
Hs Code.:

Synonyms:(3aR,4R,5R,6aS)-4-[(3R)-(tert-butyldimethylsilyl)oxy-5-phenylpentyl]perhydrocyclopenta[b]furan-2,5-diol

Suppliers and Price of (3aR,4R,5R,6aS)-4-[(3R)-(tert-butyldimethylsilyl)oxy-5-phenylpentyl]perhydrocyclopenta[b]furan-2,5-diol

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Total 2 raw suppliers

Chemical Property of (3aR,4R,5R,6aS)-4-[(3R)-(tert-butyldimethylsilyl)oxy-5-phenylpentyl]perhydrocyclopenta[b]furan-2,5-diol

Chemical Property:

Purity/Quality:: 98% min ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

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Technology Process of (3aR,4R,5R,6aS)-4-[(3R)-(tert-butyldimethylsilyl)oxy-5-phenylpentyl]perhydrocyclopenta[b]furan-2,5-diol

There total 10 articles about (3aR,4R,5R,6aS)-4-[(3R)-(tert-butyldimethylsilyl)oxy-5-phenylpentyl]perhydrocyclopenta[b]furan-2,5-diol 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: 64.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 155206-00-1
bimatoprost

: 1393740-68-5
(3aR,4R,5R,6aS)-4-[(3R)-(tert-butyldimethylsilyl)oxy-5-phenylpentyl]perhydrocyclopenta[b]furan-2,5-diol

Guidance literature:: bimatoprost; With butylboronic acid; In dichloromethane; for 0.666667h; Reflux;

t-butyldimethylsiyl triflate; With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; Cooling with ice;

Reference yield:

: 865087-12-3
(3aR,4R,5R,6aS)-4-[3S-(t-butyldimethylsiloxy)-5-phenyl-1E-pentenyl]-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-ol

: 1201226-16-5
(5-(ethylamino)-5-oxopentyl)triphenylphosphonium bromide

: 1393740-68-5
(3aR,4R,5R,6aS)-4-[(3R)-(tert-butyldimethylsilyl)oxy-5-phenylpentyl]perhydrocyclopenta[b]furan-2,5-diol

Guidance literature:: (5-(ethylamino)-5-oxopentyl)triphenylphosphonium bromide; With valerianate de potassium; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere; Schlenk technique;

(3aR,4R,5R,6aS)-4-[3S-(t-butyldimethylsiloxy)-5-phenyl-1E-pentenyl]-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-ol; In tetrahydrofuran; at 0 - 20 ℃; for 4h; Inert atmosphere; Schlenk technique;
DOI:10.1021/ol503520f

Reference yield:

: (S)-5-((tert-butyldimethylsilyl)oxy)-2-methyl-7-phenylhept-3-yn-2-ol

: 1393740-68-5
(3aR,4R,5R,6aS)-4-[(3R)-(tert-butyldimethylsilyl)oxy-5-phenylpentyl]perhydrocyclopenta[b]furan-2,5-diol

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydride / toluene; mineral oil / 20 h / Reflux

2.1: Schwartz's reagent / dichloromethane / 1 h / 20 °C / Inert atmosphere; Schlenk technique

2.2: 1 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

3.1: tert.-butyl lithium / diethyl ether; pentane / 4 h / -78 - -40 °C / Inert atmosphere; Schlenk technique

3.2: 0.5 h / -30 °C / Inert atmosphere; Schlenk technique

4.1: ozone / methanol; dichloromethane / -78 °C

4.2: -78 - 20 °C

5.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C

6.1: valerianate de potassium / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Schlenk technique

6.2: 4 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

With Schwartz's reagent; tert.-butyl lithium; valerianate de potassium; sodium hydride; diisobutylaluminium hydride; ozone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; mineral oil; pentane;
DOI:10.1021/ol503520f