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

Base Information

• Chemical Name: (3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol
• CAS No.: 155899-66-4
• Molecular Formula: C8H15NO3
• Molecular Weight: 173.212
• Hs Code.: 2932990090
• European Community (EC) Number: 692-595-4
• DSSTox Substance ID: DTXSID10438496
• Nikkaji Number: J830.785G
• Wikidata: Q72442275
• Mol file: 155899-66-4.mol

Synonyms:155899-66-4;(3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol;(3AR,4S,6R,6AS)-6-AMINOTETRAHYDRO-2,2-DIMETHYL-4H-CYCLOPENTA-1,3-DIOXOL-4-OL;(3aR,4S,6R,6aS)-6-amino-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-ol;1265919-27-4;(3aR,4S,6R,6aS)-6-amino-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol;MFCD20527303;SCHEMBL1509195;DTXSID10438496;CS-M2377;AKOS016011584;AM85608;EX-5979;4H-CYCLOPENTA-1,3-DIOXOL-4-OL, 6-AMINOTETRAHYDRO-2,2-DIMETHYL-, (3AR,4S,6R,6AS)-;AS-39011;EN300-7401460;A850993;Q-101072;(1beta)-3beta-Amino-4alpha,5alpha-(isopropylidenedioxy)cyclopentanol;(3aR,4S,6R,6aS)-6-amino-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol

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

Chemical Property:

• Melting Point: 85-88 °C
• Boiling Point: 287.988 °C at 760 mmHg
• PKA: 14.03±0.60(Predicted)
• Flash Point: 127.971 °C
• PSA: 64.71000
• Density: 1.17 g/cm³
• LogP: 0.29870
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 173.10519334
• Heavy Atom Count: 12
• Complexity: 195

Purity/Quality:

99% ^*data from raw suppliers

(3aR,4S,6R,6aS)-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:

• Canonical SMILES: CC1(OC2C(CC(C2O1)O)N)C
• Isomeric SMILES: CC1(O[C@H]2[C@@H](C[C@@H]([C@H]2O1)O)N)C
• Uses: (3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol was used to preapare AZD6140 as an orally active reversible P2Y12 receptor antagonist for prevention of thrombosis.

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

There total 46 articles about (3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][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: 100.0%

tetrahydro-2,2-dimethyl-6-phenylmethyl-(3aS,4S,7R,7aS)-4,7-methano-4H-1,3-dioxolo[4,5-d][1,2]oxazine (155855-51-9) → (3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol (155899-66-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 30 ℃; for 18h; under 2250.23 Torr;

Reference yield: 99.0%

4,4-dimethyl-3,5,8-trioxa-9-aza-tricyclo[5.2.1.02,6]decane → (3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol (155899-66-4)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In methanol; at 20 ℃; for 1h; under 2280.15 Torr;

Reference yield: 95.8%

(3aS,4R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-amine → (3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol (155899-66-4)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In ethanol; at 20 ℃; under 1034.32 - 3102.97 Torr;

upstream raw materials:

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

(1S,2R,3S,4R)-4-O-benzylhydroxylamino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol

(1S,4R,5S,6R)-2,3-oxazabicyclo[2.2.1]heptane-5,6-dioxy-isopropylidene

2-((3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl)isoindoline-1,3-dione

Downstream 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 2-(6-(benzyloxycarbonylamino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy) acetate

(3aR,4S,6R,6aS)-6-((5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl)amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol

2-({(3aR,4S,6R,6aS)-6-[7-chloro-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-3-yl]-2,2-dimethyltetrahydro-3aH-cyclopentadiene[d][1,3]dioxolene-4-yl}oxy)ethanol