Acetic acid, [[(3aR,4S,6R,6aS)-tetrahydro-2,2-diMethyl-6-[[(phenylMethoxy)carbonyl]aMino]-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-, ethyl ester

Base Information

• Chemical Name: Acetic acid, [[(3aR,4S,6R,6aS)-tetrahydro-2,2-diMethyl-6-[[(phenylMethoxy)carbonyl]aMino]-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-, ethyl ester
• CAS No.: 866551-95-3
• Molecular Formula: C₂₀H₂₇NO₇
• Molecular Weight: 393.437
• Mol file: 866551-95-3.mol

Synonyms:Acetic acid, [[(3aR,4S,6R,6aS)-tetrahydro-2,2-diMethyl-6-[[(phenylMethoxy)carbonyl]aMino]-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-, ethyl ester

Chemical Property of Acetic acid, [[(3aR,4S,6R,6aS)-tetrahydro-2,2-diMethyl-6-[[(phenylMethoxy)carbonyl]aMino]-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-, ethyl ester

Chemical Property:

• Boiling Point: 540.7±50.0 °C(Predicted)
• PKA: 11.26±0.60(Predicted)
• PSA: 92.32000
• Density: 1.24±0.1 g/cm3(Predicted)
• LogP: 2.54440
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99.99%HPLC ^*data from raw suppliers

Ethyl2-[[(3aR,4S,6R,6aS)-6-[(Benzyloxycarbonyl)amino]-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]oxy]acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Ethyl 2-[[(3aR,4S,6R,6aS)-6-[(Benzyloxycarbonyl)amino]-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]oxy]acetate is used as a reactant in the synthesis of Ticagrelor (T437700), a platelet aggregation inhibitor.

Technology Process of Acetic acid, [[(3aR,4S,6R,6aS)-tetrahydro-2,2-diMethyl-6-[[(phenylMethoxy)carbonyl]aMino]-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-, ethyl ester

There total 30 articles about Acetic acid, [[(3aR,4S,6R,6aS)-tetrahydro-2,2-diMethyl-6-[[(phenylMethoxy)carbonyl]aMino]-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-, ethyl ester 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: 69.0%

[3aS-(3aα,4α,6α,6aα)]-(tetrahydro-6-hydroxy-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl)carbamic acid phenylmethyl ester (274693-53-7) + ethyl bromoacetate (105-36-2) → ethyl 2-(6-(benzyloxycarbonylamino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy) acetate (866551-95-3)

Guidance literature:

[3aS-(3aα,4α,6α,6aα)]-(tetrahydro-6-hydroxy-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl)carbamic acid phenylmethyl ester; With sodium hydride; In N,N-dimethyl-formamide; at -30 ℃; for 0.5h;

ethyl bromoacetate; In N,N-dimethyl-formamide; at 20 ℃; for 5.5h;

Reference yield: 34.0%

benzyl ((3aS,4R,6R,6aR)-6-hydroxy-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl)carbamate (1423769-49-6) + ethyl bromoacetate (105-36-2) → ethyl 2-(((3aR,4R,6R,6aS)-6-(((benzyloxy)carbonyl)amino)-2,2-dimethyltetrahydro-4H-cyclopenta[d]-[1,3]dioxol-4-yl)oxy)acetate (866551-95-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃;

DOI:10.1016/j.tetlet.2015.09.074

Reference yield:

(3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol (155899-66-4) → ethyl 2-(6-(benzyloxycarbonylamino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy) acetate (866551-95-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium carbonate / water; tetrahydrofuran / 0 °C

2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C

2.2: 5.5 h / 20 °C

With sodium hydride; sodium carbonate; In tetrahydrofuran; water; N,N-dimethyl-formamide;

upstream raw materials:

[3aS-(3aα,4α,6α,6aα)]-(tetrahydro-6-hydroxy-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl)carbamic acid phenylmethyl ester

ethyl bromoacetate

(3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol

N-(((4S,5R)-2,2-dimethyl-5-vinyl-1 ,3-dioxolan-4-yl)methylene)-1-phenylmethanamine oxide

Downstream raw materials:

(1S 2S,3R,5S)-3-[(5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl)amino]-5-(2-hydroxyethoxy)cyclopentane-1,2-diol

Refernces

• 1、 Mahender, Madaraboina,Yakambaram,Pandey, Jaya,Chandrashekar,Reddy, L. Amarnath,Jayashree,Bandichhor, Rakeshwar. "Stereoselective Synthesis for Potential Isomers of Ticagrelor Key Starting Material". . p. 2866 - 2872. Retrieved 2019/08/30.
• 2、 Zhang, Hao,Liu, Jun,Zhang, Luyong,Kong, Lingyi,Yao, Hequan,Sun, Hongbin. "Synthesis and biological evaluation of ticagrelor derivatives as novel antiplatelet agents". supporting information; experimental part. p. 3598 - 3602. Retrieved 2012/07/14.