2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol L-tataric acid

Base Information

• Chemical Name: 2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol L-tataric acid
• CAS No.: 376608-65-0
• Molecular Formula: C16H29NO12
• Molecular Weight: 367.353
• Hs Code.: 29329990
• Mol file: 376608-65-0.mol

Synonyms:2-(((3aR,4S,6R,6aS)-6-Amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol (2R,3R,4S,5R)-2,3,4,5-tetrahydroxyhexanedioate;2-[[(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-ethanol (2R,3R)-2,3-dihydroxybutanedioate;

Chemical Property of 2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol L-tataric acid

Chemical Property:

• PSA: 189.00000
• LogP: -1.80730
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature

Purity/Quality:

99% ^*data from raw suppliers

2-[[(3aR,4S,6R,6aS)-6-aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-Ethanol(2R,3R)-2,3-dihydroxybutanedioate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-[[(3aR,4S,6R,6aS)-6-aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-Ethanol (2R,3R)-2,3-dihydroxybutanedioate is a useful building block, most frequently used in the preparation of the antithrombotic agent Ticagrelor.

Technology Process of 2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol L-tataric acid

There total 13 articles about 2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol L-tataric 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: 87.47%

benzyl 6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ylcarbamate (274693-54-8) + L-Tartaric acid (87-69-4,138508-61-9) → 2-[[(3aR,4S,6R,6aS)-6-aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol (2R,3R)-2,3-dihydroxybutanedioic acid (376608-65-0)

Guidance literature:

benzyl 6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ylcarbamate; With palladium 10% on activated carbon; ammonium formate; In methanol; at 20 - 50 ℃; for 10h;

L-Tartaric acid; at 10 - 50 ℃; for 3h;

Reference yield:

[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol (274693-55-9) + L-Tartaric acid (87-69-4,138508-61-9) → 2-[[(3aR,4S,6R,6aS)-6-aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol (2R,3R)-2,3-dihydroxybutanedioic acid (376608-65-0)

Guidance literature:

at 20 - 40 ℃; for 21h;

Reference yield:

[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) → 2-[[(3aR,4S,6R,6aS)-6-aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol (2R,3R)-2,3-dihydroxybutanedioic acid (376608-65-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -20 °C

1.2: 6.33 h / -20 - 20 °C

2.1: sodium tetrahydroborate; ethanol / 4 h / 60 °C

3.1: ammonium formate; palladium 10% on activated carbon / ethanol / 1 h / 40 °C

4.1: 21 h / 20 - 40 °C

With sodium tetrahydroborate; ethanol; palladium 10% on activated carbon; ammonium formate; sodium hydride; In ethanol; N,N-dimethyl-formamide;

upstream raw materials:

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

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

β-D-ribofuranose

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

Downstream raw materials:

2-[[(3aR,4S,6R,6aS)-6-[[4-[N-[(1R,2S)-2-(3,4-difluorophenyl)cyclopropan-1-yl]-N-tert-butoxycarbonyl]amino]-2-(propylthio)-5-nitropyrimidin-6-yl]-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]oxy] ethanol

Refernces

• 1、 -. "Method for preparing ticagrelor key intermediate". . . Retrieved 2017/02/17.