(1R, 3S, 4R)-3-Benzyloxy-4-(benzyloxymethyl)cyclopentanamine

Base Information

• Chemical Name: (1R, 3S, 4R)-3-Benzyloxy-4-(benzyloxymethyl)cyclopentanamine
• CAS No.: 114826-86-7
• Molecular Formula: C20H25 N O2
• Molecular Weight: 311.424
• Mol file: 114826-86-7.mol

Synonyms:Cyclopentanamine,3-(phenylmethoxy)-4-[(phenylmethoxy)methyl]-, [1R-(1a,3b,4a)]-

Chemical Property of (1R, 3S, 4R)-3-Benzyloxy-4-(benzyloxymethyl)cyclopentanamine

Chemical Property:

• PSA: 44.48000
• LogP: 4.22620

Purity/Quality:

99%min ^*data from raw suppliers

(1R,3S,4R)-3-BENZYLOXY-4-(BENZYLOXYMETHYL)CYCLOPENTANAMINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R, 3S, 4R)-3-Benzyloxy-4-(benzyloxymethyl)cyclopentanamine

There total 28 articles about (1R, 3S, 4R)-3-Benzyloxy-4-(benzyloxymethyl)cyclopentanamine 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: 43.0%

(1R,3S,4R)-1-azido-3-benzyloxy-4-benzyloxymethylcyclopentane → (1R, 3S, 4R)-1-amino-3-benzyloxy-4-(benzyloxymethyl)cyclopentane (114826-86-7)

Guidance literature:

With tri-n-butyl-tin hydride; In benzene; for 1.5h; Heating;

DOI:10.1016/S0040-4039(01)91379-6

Reference yield:

(1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one (34638-25-0,38110-77-9,43119-28-4,54483-22-6,26054-46-6) → (1R, 3S, 4R)-1-amino-3-benzyloxy-4-(benzyloxymethyl)cyclopentane (114826-86-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 1) H₂SO₄, AcOH; / 1) 60 deg C, 1 day; 2) Amberlite IR-120(H⁺), 70 deg C, 15 h

2: 60 percent / NaH / dimethylformamide

4: 73 percent / LDA, MoOPH / tetrahydrofuran / -78 - 20 °C

5: 69 percent / LiAlH₄ / diethyl ether / 3 h / Ambient temperature

6: 83 percent / NaIO₄ / H₂O; acetone / 0.25 h / Ambient temperature

7: 76 percent / PDC / dimethylformamide / 19 h / Ambient temperature

8: 67 percent / iodobenzenediacetate, I₂ / CCl₄ / 0.25 h / Heating; Irradiation

9: 99 percent / N-Bu₃SnH / diethyl ether / 10 h / Heating

10: 74 percent / p-TsOH / methanol / 0.67 h / Ambient temperature

11: 71 percent / (PhO)2P(O)N₃,Ph₃P, (NCO₂Et)2 / tetrahydrofuran / 0.17 h / Ambient temperature

12: 43 percent / n-Bu₃SnH / benzene / 1.5 h / Heating

With sodium periodate; lithium aluminium tetrahydride; dipyridinium dichromate; MoO₅*pyridine*HMPA; [bis(acetoxy)iodo]benzene; sulfuric acid; diphenyl phosphoryl azide; iodine; tri-n-butyl-tin hydride; sodium hydride; toluene-4-sulfonic acid; acetic acid; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; water; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/S0040-4039(01)91379-6

Reference yield:

tert-butyl ((1R,3S,4R)-3-benzyloxy-4-benzyloxymethylbicyclo[3.1.0]hexan-1-yl)carbamate (1177260-52-4) → (1R, 3S, 4R)-1-amino-3-benzyloxy-4-(benzyloxymethyl)cyclopentane (114826-86-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1002/anie.201904794

upstream raw materials:

(3R,4S)-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]cyclopent-1-ene

Benzyloxymethyl chloride

5-(benzyloxymethyl)cyclopentadiene

cyclopenta-1,3-diene

Downstream raw materials:

1-((1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl)-5-methylpyrimidine-2,4(1H,3H)-dione

Refernces

• 1、 Wildenhof, Thomas M.,Schiffers, Sarah,Traube, Franziska R.,Mayer, Peter,Carell, Thomas. "Influencing Epigenetic Information with a Hydrolytically Stable Carbocyclic 5-Aza-2′-deoxycytidine". supporting information. p. 12984 - 12987. Retrieved 2019/08/02.
• 2、 Otvos,Beres,Sagi,Tomoskozi,Gruber. "The first stereospecific synthesis of (+)-(1R, 2S, 4R)-4-amino-2-hydroxy-1-cyclopentanemethanol and (+)-carbocyclic thymidine". . p. 6381 - 6384,6381-6384. Retrieved 2007/10/02.