(3aS,4R,6S,6aR)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol

Base Information

• Chemical Name: (3aS,4R,6S,6aR)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol
• CAS No.: 592533-90-9
• Molecular Formula: C8H15NO3
• Molecular Weight: 173.21
• Mol file: 592533-90-9.mol

Synonyms:Ticagrelor Related Compound 2 ((3aS, 4R, 6S, 6aR)-6-Aminotetrahydro-2,2-Dimethyl-4H-Cyclopenta-1.3-dioxol-4-ol);

Chemical Property of (3aS,4R,6S,6aR)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol

Chemical Property:

• Boiling Point: 288.0±40.0 oC (760 Torr)
• PKA: 14.03±0.60(Predicted)
• Flash Point: 128.0±27.3 oC
• PSA: 64.71000
• Density: 1.170±0.06 g/cm3 (20 oC 760 Torr)
• LogP: 0.29870

Purity/Quality:

98%,99%, ^*data from raw suppliers

(3aS,4R,6S,6aR)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (3aS,4R,6S,6aR)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol is used as a reagent to synthesize (3S,4R,5S)-(+)-3-amino-4,5-dihydroxycyclopentene for use as a chiral synthon toward carbocyclic nucleosides.

Technology Process of (3aS,4R,6S,6aR)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol

There total 10 articles about (3aS,4R,6S,6aR)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-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:

(1S,2R,6R,7R)-4,4-Dimethyl-3,5,8-trioxa-9-aza-tricyclo[5.2.1.02,6]decane (592533-89-6) → (3aS,4R,6S,6aR)-6-Amino-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol (592533-90-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 0.5h;

DOI:10.1016/S0040-4039(00)01668-3

Reference yield:

(1R,4S)-N--2,3-oxazabicyclo<2.2.1>hept-5-ene (160167-61-3) → (3aS,4R,6S,6aR)-6-Amino-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol (592533-90-9)

Guidance literature:

Multi-step reaction with 4 steps

1: OsO₄; NMO / tetrahydrofuran; H₂O

2: p-TsOH

3: NaBH₄ / methanol

4: H₂ / Pd/C / methanol

With sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; water;

DOI:10.1016/S0040-4039(03)00973-0

Reference yield:

[(S)-2-((1R,4S,5R,6R)-5,6-Dihydroxy-2-oxa-3-aza-bicyclo[2.2.1]hept-3-yl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester → (3aS,4R,6S,6aR)-6-Amino-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol (592533-90-9)

Guidance literature:

Multi-step reaction with 3 steps

1: p-TsOH

2: NaBH₄ / methanol

3: H₂ / Pd/C / methanol

With sodium tetrahydroborate; hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol;

DOI:10.1016/S0040-4039(03)00973-0

upstream raw materials:

(1S,2R,6R,7R)-4,4-Dimethyl-3,5,8-trioxa-9-aza-tricyclo[5.2.1.0^2,6]decane

2-((1S,4R)-4-hydroxycyclopent-2-en-1-yl)isoindoline-1,3-dione

(1S,4R)-4-hydroxy-2-cyclopenten-1-yl diethyl phosphate

cyclopenta-1,3-diene

Refernces

• 1、 Yin, Xueqiang,Schneller, Stewart W. "L-deaza-5'-noraisteromycin.". . p. 67 - 76. Retrieved 2007/10/03.