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

Base Information

• Chemical Name: Benzyl ((3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)carbamate
• CAS No.: 274693-53-7
• Molecular Formula: C16H21 N O5
• Molecular Weight: 307.346
• European Community (EC) Number: 700-846-7
• DSSTox Substance ID: DTXSID70477487
• Nikkaji Number: J2.688.931F
• Wikidata: Q72505689
• Mol file: 274693-53-7.mol

Synonyms:274693-53-7;Benzyl ((3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)carbamate;CarbaMicacid,N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-diMethyl-4H-cyclopenta-1,3-dioxol-4-yl]-,phenylMethyl ester;benzyl (3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ylcarbamate;Benzyl [(3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]carbamate;benzyl N-[(3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]carbamate;N-[(3aS,4R,6S,6aR)-Tetrahydro-6-hydroxy-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]carbamicacid phenylmethyl ester;benzyl N-[(3aR,4S,6R,6aS)-4-hydroxy-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-6-yl]carbamate;benzyl (3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ylcarbamate;MFCD21362984;SCHEMBL10249662;DTXSID70477487;VPICQZQITAJOQA-ZOBORPQBSA-N;CS-M1243;AKOS016005436;AM85694;[3aS-(3aalpha,4alpha,6alpha,6aalpha)]- (tetrahydro-6-hydroxy-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl)carbamic acid phenylmethyl ester;AC-26975;Benzyl((3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)carbamate;DS-18326;NS00002960;P20891;EN300-7419539;A846830;Benzyl (3 aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ylcarbamate;Benzyl [(3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyltetra-hydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]carbamate;Benzyl [(3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydro-2H,3aH-cyclopenta[d][1,3]dioxol-4-yl]carbamate;Benzyl [(3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,31dioxol-4-yl]carbamate;Phenylmethyl ester N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]-Carbamic acid;phenylmethyl N-[(3aS, 4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]-carbamate

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

Chemical Property:

• Boiling Point: 489.1±45.0 °C(Predicted)
• PKA: 11.41±0.60(Predicted)
• PSA: 80.51000
• Density: 1.28
• LogP: 1.77050
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 307.14197277
• Heavy Atom Count: 22
• Complexity: 407

Purity/Quality:

99%min ^*data from raw suppliers

PhenylmethylesterN-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]-Carbamicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(CC(C2O1)O)NC(=O)OCC3=CC=CC=C3)C
• Isomeric SMILES: CC1(O[C@H]2[C@@H](C[C@@H]([C@H]2O1)O)NC(=O)OCC3=CC=CC=C3)C
• Uses: Phenylmethyl ester N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]-Carbamic acid is a useful chiral building block. It has been used in the synthesis of all-cis carbocyclic precursor of ticagrelor via oxidation/stereoselective reduction sequences.

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

There total 19 articles about Benzyl ((3aS,4R,6S,6aR)-6-hydroxy-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: 95.0%

benzyl chloroformate (501-53-1,94274-21-2) + (3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol (155899-66-4) → [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)

Guidance literature:

With N-ethyl-N,N-diisopropylamine;

DOI:10.1016/j.bmcl.2007.07.057

Reference yield: 77.0%

C8H15NO3*C18H12Cl2O8 + benzyl chloroformate (501-53-1,94274-21-2) → [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)

Guidance literature:

C₈H₁₅NO₃*C₁₈H₁₂Cl₂O₈; With sodium hydroxide; In water; toluene; at 20 ℃; for 0.5h;

benzyl chloroformate; In water; toluene; at 20 ℃; for 2.5h;

Reference yield:

(3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-aminium (2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoate (1413395-24-0) + benzyl chloroformate (501-53-1,94274-21-2) → [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)

Guidance literature:

(3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-aminium (2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoate; With hydrogenchloride; In ethyl acetate; at 5 ℃; for 0.416667h; pH=1 - 2;

benzyl chloroformate; With potassium carbonate; In water; 4-methyl-2-pentanone; at 20 - 30 ℃; for 0.666667h;

upstream raw materials:

benzyl chloroformate

(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

methyl 2,3-O-isopropylidene-D-ribofuranoside

Downstream raw materials:

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

benzyl 6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ylcarbamate

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

Refernces

• 1、 -. "Preparation method of ticagrelor key chiral intermediate isomer impurity TGAD1". Paragraph 0033-0035. . Retrieved 2021/10/02.
• 2、 -. "Method for preparing ticagrelor key intermediate". Paragraph 0023; 0046. . Retrieved 2017/02/17.