(2R,3S,5S)-3-(Benzyloxy)-5-[2-[[(4-methoxyphenyl)diphenylmethyl]amino]-6-(phenylmethoxy)-9H-purin-9-yl]-2-(benzyloxymethyl)cyclopentanol

Base Information

• Chemical Name: (2R,3S,5S)-3-(Benzyloxy)-5-[2-[[(4-methoxyphenyl)diphenylmethyl]amino]-6-(phenylmethoxy)-9H-purin-9-yl]-2-(benzyloxymethyl)cyclopentanol
• CAS No.: 142217-78-5
• Molecular Formula: C52H49N5O5
• Molecular Weight: 823.992
• Mol file: 142217-78-5.mol

Synonyms:Entecavir-4

Chemical Property of (2R,3S,5S)-3-(Benzyloxy)-5-[2-[[(4-methoxyphenyl)diphenylmethyl]amino]-6-(phenylmethoxy)-9H-purin-9-yl]-2-(benzyloxymethyl)cyclopentanol

Chemical Property:

• Appearance/Colour: Colorless transparent liquid
• Refractive Index: 1.645
• PKA: 13.87±0.70(Predicted)
• PSA: 112.78000
• Density: 1.23 g/cm³
• LogP: 9.61500
• Storage Temp.: 2-8°C
• Solubility.: Acetonitrile (Slightly, Sonicated), DMSO (Slightly, Sonicated), Methanol (Slight

Purity/Quality:

99.0% ^*data from raw suppliers

Entecavirinter-4 >95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Entecavir-?5 is used in the preparation of the anti-?HBV drug Entecavir.

Technology Process of (2R,3S,5S)-3-(Benzyloxy)-5-[2-[[(4-methoxyphenyl)diphenylmethyl]amino]-6-(phenylmethoxy)-9H-purin-9-yl]-2-(benzyloxymethyl)cyclopentanol

There total 8 articles about (2R,3S,5S)-3-(Benzyloxy)-5-[2-[[(4-methoxyphenyl)diphenylmethyl]amino]-6-(phenylmethoxy)-9H-purin-9-yl]-2-(benzyloxymethyl)cyclopentanol 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: 82.0%

[1S-(1α,2β,3α,5β)]-5-(2-amino-6-benzyloxy-9H-purin-9-yl)-3-benzyloxy-2-(benzyloxy)methyl-cyclopentanol (142217-77-4) + mono-4-methoxytrityl chloride (14470-28-1) → (1S,2S,3S,5S)-5-[2-[[(4-methoxyphenyl)diphenylmethyl]amino]-6-benzyloxy-9H-purin-9-yl]-3-benzyloxy-2-[(benzyloxy)methyl]cyclopentanol (142217-78-5)

Guidance literature:

With dmap; TEA; In dichloromethane;

DOI:10.1016/S0960-894X(96)00594-X

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → (1S,2S,3S,5S)-5-[2-[[(4-methoxyphenyl)diphenylmethyl]amino]-6-benzyloxy-9H-purin-9-yl]-3-benzyloxy-2-[(benzyloxy)methyl]cyclopentanol (142217-78-5)

Guidance literature:

Multi-step reaction with 6 steps

1: tetrahydrofuran / -78 - -65 °C

2: 1.) diisopinylcampheylborane (prepared from (+)-α-pinene), 2.) aq. NaOH, H2O2 / 1.) THF, -65 to -78 deg C

3: VO(acac)2, t-BuOOH / CH₂Cl₂

4: NaH, Bu₄NI / dimethylformamide

5: 60 percent / LiH / dimethylformamide / 2 h / 125 °C

6: 82 percent / TEA, DMAP / CH₂Cl₂

With tert.-butylhydroperoxide; dmap; sodium hydroxide; bis(acetylacetonate)oxovanadium; (-)-diisopinocampheylborane; TEA; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; lithium hydride; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(96)00594-X

Reference yield:

5-(benzyloxymethyl)cyclopentadiene (39939-07-6) → (1S,2S,3S,5S)-5-[2-[[(4-methoxyphenyl)diphenylmethyl]amino]-6-benzyloxy-9H-purin-9-yl]-3-benzyloxy-2-[(benzyloxy)methyl]cyclopentanol (142217-78-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) diisopinylcampheylborane (prepared from (+)-α-pinene), 2.) aq. NaOH, H2O2 / 1.) THF, -65 to -78 deg C

2: VO(acac)2, t-BuOOH / CH₂Cl₂

3: NaH, Bu₄NI / dimethylformamide

4: 60 percent / LiH / dimethylformamide / 2 h / 125 °C

5: 82 percent / TEA, DMAP / CH₂Cl₂

With tert.-butylhydroperoxide; dmap; sodium hydroxide; bis(acetylacetonate)oxovanadium; (-)-diisopinocampheylborane; TEA; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; lithium hydride; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(96)00594-X

upstream raw materials:

[1S-(1α,2β,3α,5β)]-5-(2-amino-6-benzyloxy-9H-purin-9-yl)-3-benzyloxy-2-(benzyloxy)methyl-cyclopentanol

mono-4-methoxytrityl chloride

Benzyloxymethyl chloride

5-(benzyloxymethyl)cyclopentadiene

Downstream raw materials:

2-amino-1,9-dihydro-9-<<1S-(1α,2α,3α,4β)>-2-fluoro-4-hydroxy-3-(hydroxymethyl)cyclopentyl>-6H-purin-6-one

Refernces

• 1、 Bisacchi,Chao,Bachard,Daris,Innaimo,Jacobs,Kocy,Lapointe,Martel,Merchant,Slusarchyk,Sundeen,Young,Colonno,Zahler. "BMS-200475, a novel carbocyclic 2'-deoxyguanosine analog with potent and selective anti-hepatitis B virus activity in vitro". . p. 127 - 132. Retrieved 2007/10/03.