Benzyl ((3aS,4R,6S,6aR)-6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)carbamate

Base Information

• Chemical Name: Benzyl ((3aS,4R,6S,6aR)-6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)carbamate
• CAS No.: 274693-54-8
• Molecular Formula: C18H25NO6
• Molecular Weight: 351.4
• DSSTox Substance ID: DTXSID701106755
• Mol file: 274693-54-8.mol

Synonyms:274693-54-8;Benzyl ((3aS,4R,6S,6aR)-6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)carbamate;CID 9924588;benzyl N-[(3aR,4S,6R,6aS)-4-(2-hydroxyethoxy)-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-6-yl]carbamate;N-[(3aS,4R,6S,6aR)-Tetrahydro-6-(2-hydroxyethoxy)-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]carbamic acid phenylmethyl ester;n-((3as,4r,6s,6ar)-tetrahydro-6-(2-hydroxyethoxy)-2,2-dimethyl-4h-cyclopenta-1,3-dioxol-4-yl)carbamic acid phenylmethyl ester;SCHEMBL10249654;DTXSID701106755;CS-M2434;ZKA69354;MFCD22419928;DS-19240;BENZYL ((3AS,4R,6S,6AR)-6-(2-HYDROXYETHOXY)-2,2-DIMETHYLTETRAHYDRO-4H-CYCLOPENTA[D][1,3]DIOXOL-4-YL)CARBAMATE;Phenylmethyl N-[(3aS,4R,6S,6aR)-tetrahydro-6-(2-hydroxyethoxy)-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]carbamate

Chemical Property of Benzyl ((3aS,4R,6S,6aR)-6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)carbamate

Chemical Property:

• Boiling Point: 524.6±50.0 °C(Predicted)
• PKA: 11.29±0.60(Predicted)
• PSA: 86.25000
• Density: 1.26
• LogP: 1.97360
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 351.16818752
• Heavy Atom Count: 25
• Complexity: 451

Purity/Quality:

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

Benzyl((3aS,4R,6S,6aR)-6-(2-Hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)carbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(CC(C2O1)OCCO)NC(=O)OCC3=CC=CC=C3)C
• Isomeric SMILES: CC1(O[C@H]2[C@@H](C[C@@H]([C@H]2O1)OCCO)NC(=O)OCC3=CC=CC=C3)C

Technology Process of Benzyl ((3aS,4R,6S,6aR)-6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)carbamate

There total 22 articles about Benzyl ((3aS,4R,6S,6aR)-6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)carbamate 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: 91.1%

ethyl 2-(6-(benzyloxycarbonylamino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy) acetate (866551-95-3) → benzyl 6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ylcarbamate (274693-54-8)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; at 0 ℃; for 5h;

DOI:10.1016/j.bmcl.2012.04.050

Reference yield:

C21H27NO9 → benzyl 6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ylcarbamate (274693-54-8)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; at 0 - 10 ℃; for 4h;

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) + ethyl bromoacetate (105-36-2) → benzyl 6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ylcarbamate (274693-54-8)

Guidance literature:

With lithium borohydride; potassium tert-butylate; In tetrahydrofuran; water; acetic acid;

upstream raw materials:

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

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

ethyl bromoacetate

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

Downstream raw materials:

[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

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

2-[((3aR,4S,6R,6aS)-6-[[5-amino-6-chloro-2-(propylsulfanyl)-4-pyrimidinyl]amino]-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy]-1-ethanol

ticagrelor

Refernces

• 1、 -. "Method for preparing ticagrelor key intermediate". Paragraph 0025; 0048. . Retrieved 2017/02/17.
• 2、 -. "NEW INTERMEDIATES AND PROCESSES FOR PREPARING TICAGRELOR". Page/Page column 79. . Retrieved 2012/10/18.