(2S,3R,4S)-2-(hydroxymethyl)-4-[(11R)-11-hydroxy-13-methyltetradecyl]azetidin-3-ol

Base Information

• Chemical Name: (2S,3R,4S)-2-(hydroxymethyl)-4-[(11R)-11-hydroxy-13-methyltetradecyl]azetidin-3-ol
• CAS No.: 135574-63-9
• Molecular Formula: C19H39NO3
• Molecular Weight: 329.5179
• Mol file: 135574-63-9.mol

Synonyms:

Chemical Property of (2S,3R,4S)-2-(hydroxymethyl)-4-[(11R)-11-hydroxy-13-methyltetradecyl]azetidin-3-ol

Chemical Property:

• Vapor Pressure: 2.62E-11mmHg at 25°C
• Boiling Point: 481.8°Cat760mmHg
• Flash Point: 84.1°C
• Density: 0.989g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S)-2-(hydroxymethyl)-4-[(11R)-11-hydroxy-13-methyltetradecyl]azetidin-3-ol

There total 61 articles about (2S,3R,4S)-2-(hydroxymethyl)-4-[(11R)-11-hydroxy-13-methyltetradecyl]azetidin-3-ol 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: 92.0%

tert-butyl (2S,3R,4S)-3-hydroxy-2-hydroxymethyl-4-[(11S)-11-hydroxy-13-methyltetradecyl]azetidine-1-carboxylate (190438-31-4) → penaresidin B (135574-63-9)

Guidance literature:

With hydrogenchloride; In methanol; water; at 0 - 20 ℃; for 2h;

DOI:10.1016/j.tet.2018.07.023

Reference yield:

(S)-14-((2S,3R,4S)-3-hydroxy-4-(hydroxymethyl)-1-(phenoxysulfonyl)azetidin-2-yl)-2-methyltetradecan-4-yl-4-nitrobenzoate → penaresidin B (135574-63-9)

Guidance literature:

(S)-14-((2S,3R,4S)-3-hydroxy-4-(hydroxymethyl)-1-(phenoxysulfonyl)azetidin-2-yl)-2-methyltetradecan-4-yl-4-nitrobenzoate; With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); methylmagnesium bromide; In diethyl ether; benzene; at 55 ℃; for 15h; Inert atmosphere;

With hydrogenchloride; In methanol; at 55 ℃; for 6h; Solvent; Sealed tube;

DOI:10.1021/acs.orglett.9b04096

Reference yield:

2-(R)-isobutyl-oxirane (60856-89-5) → penaresidin B (135574-63-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C / Inert atmosphere

1.2: 1 h / -78 - -40 °C / Inert atmosphere

2.1: potassium hydride; Trimethylenediamine / 21 h / 0 - 20 °C / Inert atmosphere

3.1: quinoline; hydrogen / dichloromethane / 0.5 h / 0 °C / 760.05 Torr

4.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

4.2: 48 h / Reflux

5.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 3.5 h / Inert atmosphere; Reflux

6.1: caesium carbonate; thiophenol / acetonitrile / 20 - 50 °C / Inert atmosphere

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

8.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 7600.51 Torr

9.1: hydrogenchloride / methanol; water / 2 h / 0 - 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; quinoline; hydrogenchloride; n-butyllithium; palladium 10% on activated carbon; hydrogen; potassium hydride; sodium hydride; caesium carbonate; thiophenol; Trimethylenediamine; triethylamine; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; acetonitrile; mineral oil;

DOI:10.1016/j.tet.2018.07.023

upstream raw materials:

tert-butyl (2S,3R,4S)-3-hydroxy-2-hydroxymethyl-4-[(11S)-11-hydroxy-13-methyltetradecyl]azetidine-1-carboxylate

(2S,3R,4S)-3-Methoxymethoxy-2-methoxymethoxymethyl-4-((S)-11-methoxymethoxy-13-methyl-tetradecyl)-azetidine-1-carboxylic acid tert-butyl ester

(2S,3R,4S)-3,4-Dihydroxy-2-((S)-11-methoxymethoxy-13-methyl-tetradecyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

[(1S,12S)-1-((1R,2R)-2-Hydroxy-1,3-bis-methoxymethoxy-propyl)-12-methoxymethoxy-14-methyl-pentadecyl]-carbamic acid tert-butyl ester

Refernces

• 1、 Betz, Kerry N.,Chiappini, Nicholas D.,Du Bois. "Intermolecular sp3-C-H Amination for the Synthesis of Saturated Azacycles". . p. 1687 - 1691. Retrieved 2020/01/09.
• 2、 Yoda, Hidemi,Oguchi, Tetsuhiro,Takabe, Kunihiko. "Novel asymmetric synthesis of penaresidin B as a potent actomyosin ATPase activator". . p. 3283 - 3284. Retrieved 2007/10/03.