(1S,2S,3S,5S)-5-Azido-3-(phenylMethoxy)-2-[(phenylMethoxy)Methyl]cyclopentanol

Base Information

• Chemical Name: (1S,2S,3S,5S)-5-Azido-3-(phenylMethoxy)-2-[(phenylMethoxy)Methyl]cyclopentanol
• CAS No.: 110567-23-2
• Molecular Formula: C20H23N3O3
• Molecular Weight: 353.421
• Mol file: 110567-23-2.mol

Synonyms:(1S,2S,3S,5S)-5-Azido-3-(phenylMethoxy)-2-[(phenylMethoxy)Methyl]cyclopentanol;[1S-(1α,2β,3α,5β)]-5-Αzido-3-(phenylMethoxy)-2-[(phenylMethoxy)Methyl]-cyclopentanol

Chemical Property of (1S,2S,3S,5S)-5-Azido-3-(phenylMethoxy)-2-[(phenylMethoxy)Methyl]cyclopentanol

Chemical Property:

• PSA: 88.44000
• LogP: 3.30106
• Solubility.: Dichloromethane

Purity/Quality:

97% ^*data from raw suppliers

(1S,2S,3S,5S)-5-Azido-3-(phenylmethoxy)-2-[(phenylmethoxy)methyl]cyclopentanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3S,5S)-5-Azido-3-(phenylMethoxy)-2-[(phenylMethoxy)Methyl]cyclopentanol

There total 3 articles about (1S,2S,3S,5S)-5-Azido-3-(phenylMethoxy)-2-[(phenylMethoxy)Methyl]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: 99.0%

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane (110567-22-1) → (1S,2S,3S,5S)-5-azido-3-(benzyloxy)-2-(benzyloxymethyl)cyclopentanol (110567-23-2)

Guidance literature:

With sodium azide; ammonium chloride; In ethanol; at 85 ℃; for 22h;

DOI:10.1002/jlcr.1664

Reference yield: 85.0%

(2R,3S)-3-Benzyloxy-2-benzyloxymethyl-6-oxa-bicyclo[3.1.0]hexane → (1S,2S,3S,5S)-5-azido-3-(benzyloxy)-2-(benzyloxymethyl)cyclopentanol (110567-23-2)

Guidance literature:

With sodium azide; ammonium chloride; In ethanol; water; Heating;

DOI:10.1039/C39870000255

Reference yield:

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane (110567-22-1) → (1S,2S,3S,5S)-5-azido-3-(benzyloxy)-2-(benzyloxymethyl)cyclopentanol (110567-23-2) + (1R,2R,3R,4S)-2-Azido-4-benzyloxy-3-benzyloxymethyl-cyclopentanol (117641-40-4)

Guidance literature:

With sodium azide; ammonium chloride; In ethanol; water; for 22h; Heating;

DOI:10.1039/P19880000549

upstream raw materials:

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

Downstream raw materials:

Benzoic acid (1S,2R,3S,5S)-5-azido-3-benzyloxy-2-benzyloxymethyl-cyclopentyl ester

(1S,2R,3R,4S)-1-azido-4-benzyloxy-3-benzyloxymethyl-2-fluorocyclopentane

1-((1S,2S,3R,4S)-4-Benzyloxy-3-benzyloxymethyl-2-fluoro-cyclopentyl)-1H-pyrimidine-2,4-dione

2-amino-4-methoxy-6-[(1α,2β,3α,4β)-2-hydroxy-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]cyclopentyl]amino-5-aminopyrimidine

Refernces

• 1、 Ogan, Marc D.,Kucera, David J.,Pendri, Yadagiri R.,Rinehart, J. Kent. "Synthesis of [14C]-radiolabelled entecavir". . p. 645 - 655. Retrieved 2007/10/03.
• 2、 Biggadike,Borthwick,Exall,et al.. "Synthesis of fluorinated carbocyclic nucleosides: Preparation of carbocyclic 1-(2'-deoxy-6'-fluororibofuranosyl)-5-iodouracils". . p. 255 - 256. Retrieved 2007/10/02.