(1S,2S,3S,5S)-5-(2-Amino-6-(benzyloxy)-9H-purin-9-yl)-3-(benzyloxy)-2-(benzyloxymethyl)cyclopentanol

Base Information

• Chemical Name: (1S,2S,3S,5S)-5-(2-Amino-6-(benzyloxy)-9H-purin-9-yl)-3-(benzyloxy)-2-(benzyloxymethyl)cyclopentanol
• CAS No.: 142217-77-4
• Molecular Formula: C32H33N5O4
• Molecular Weight: 551.645
• Hs Code.: 29335990
• Mol file: 142217-77-4.mol

Synonyms:Cyclopentanol,5-[2-amino-6-(phenylmethoxy)-9H-purin-9-yl]-3-(phenylmethoxy)-2-[(phenylmethoxy)methyl]-,[1S-(1a,2b,3a,5b)]- (9CI);

Chemical Property of (1S,2S,3S,5S)-5-(2-Amino-6-(benzyloxy)-9H-purin-9-yl)-3-(benzyloxy)-2-(benzyloxymethyl)cyclopentanol

Chemical Property:

• Appearance/Colour: Colorless transparent liquid
• Refractive Index: 1.67
• Boiling Point: 780.5 °C at 760 mmHg
• PKA: 13.88±0.70(Predicted)
• Flash Point: 425.8 °C
• PSA: 117.54000
• Density: 1.33 g/cm³
• LogP: 5.29280
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature

Purity/Quality:

99% ^*data from raw suppliers

(1S,2S,3S,5S)-5-(2-Amino-6-(benzyloxy)-9H-purin-9-yl)-3-(benzyloxy)-2-(benzyloxymethyl)cyclopentanol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1S,2S,3S,5S)-5-(2-Amino-6-(benzyloxy)-9H-purin-9-yl)-3-(benzyloxy)-2-(benzyloxymethyl)cyclopentanol

There total 6 articles about (1S,2S,3S,5S)-5-(2-Amino-6-(benzyloxy)-9H-purin-9-yl)-3-(benzyloxy)-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: 60.0%

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane (110567-22-1) + 2-Amino-6-benzyloxypurine (19916-73-5) → [1S-(1α,2β,3α,5β)]-5-(2-amino-6-benzyloxy-9H-purin-9-yl)-3-benzyloxy-2-(benzyloxy)methyl-cyclopentanol (142217-77-4)

Guidance literature:

With lithium hydride; In N,N-dimethyl-formamide; at 125 ℃; for 2h;

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

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → [1S-(1α,2β,3α,5β)]-5-(2-amino-6-benzyloxy-9H-purin-9-yl)-3-benzyloxy-2-(benzyloxy)methyl-cyclopentanol (142217-77-4)

Guidance literature:

Multi-step reaction with 5 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

With tert.-butylhydroperoxide; sodium hydroxide; bis(acetylacetonate)oxovanadium; (-)-diisopinocampheylborane; 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-(1α,2β,3α,5β)]-5-(2-amino-6-benzyloxy-9H-purin-9-yl)-3-benzyloxy-2-(benzyloxy)methyl-cyclopentanol (142217-77-4)

Guidance literature:

Multi-step reaction with 4 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

With tert.-butylhydroperoxide; sodium hydroxide; bis(acetylacetonate)oxovanadium; (-)-diisopinocampheylborane; 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:

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

2-Amino-6-benzyloxypurine

Benzyloxymethyl chloride

5-(benzyloxymethyl)cyclopentadiene

Downstream raw materials:

(1S,2S,3S,5S)-5-[2-[[(4-methoxyphenyl)diphenylmethyl]amino]-6-benzyloxy-9H-purin-9-yl]-3-benzyloxy-2-[(benzyloxy)methyl]cyclopentanol

2-amino-1,9-dihydro-9-[(1S,3R,4S)-2-methylene-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]cyclopentyl]-6H-purin-6-one

entecavir

(2R,3S,5S)-5-[2-[[(4-methoxyphenyl)diphenylmethyl]amino]-6-benzyloxy-9H-fluoren-9-yl]-3-benzyloxy-2-[(benzyloxy)methyl]cyclopentanone

Refernces

• 1、 -. "Method for production of entecavir intermediate IV". Paragraph 0013-0014; 0015-0016; 0017-0018. . Retrieved 2018/03/24.
• 2、 -. "Hydroxymethyl (methylenecyclopentyl) purines and pyrimidines". . . Retrieved 2008/06/13.