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

Base Information

• Chemical Name: Cyclopentanol, 3-(phenylmethoxy)-4-[(phenylmethoxy)methyl]-, (1S,3S,4R)-
• CAS No.: 114826-94-7
• Molecular Formula: C20H24O3
• Molecular Weight: 312.409
• Mol file: 114826-94-7.mol

Synonyms:

Chemical Property of Cyclopentanol, 3-(phenylmethoxy)-4-[(phenylmethoxy)methyl]-, (1S,3S,4R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Cyclopentanol, 3-(phenylmethoxy)-4-[(phenylmethoxy)methyl]-, (1S,3S,4R)-

There total 28 articles about Cyclopentanol, 3-(phenylmethoxy)-4-[(phenylmethoxy)methyl]-, (1S,3S,4R)- 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: 92.0%

(1R,3S,4R)-3-(benzyloxy)-4-[(benzyloxy)methyl]cyclopentan-1-ol (648414-59-9) → (1S,3S,4R)-3-benzyloxy-4-benzyloxymethylcyclopentan-1-ol (114826-94-7)

Guidance literature:

(1R,3S,4R)-3-benzyloxy-4-benzyloxymethylcyclopentan-1-ol; With di-isopropyl azodicarboxylate; triphenylphosphine; benzoic acid; In diethyl ether; at 0 - 20 ℃; for 16h;

With methanol; sodium hydroxide;

DOI:10.1002/chem.201200733

Reference yield: 79.0%

(3R,4S)-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]cyclopent-1-ene (191480-69-0) → (1S,3S,4R)-3-benzyloxy-4-benzyloxymethylcyclopentan-1-ol (114826-94-7) + (1R,3S,4R)-3-(benzyloxy)-4-[(benzyloxy)methyl]cyclopentan-1-ol (648414-59-9)

Guidance literature:

(3R,4S)-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]cyclopent-1-ene; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; at 20 ℃; for 12h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; ethanol; at 20 ℃; for 12h;

DOI:10.1055/s-2003-41455

Reference yield: 74.0%

2-((1S,3S,4R)-3-Benzyloxy-4-benzyloxymethyl-cyclopentyloxy)-tetrahydro-pyran (114826-93-6) → (1S,3S,4R)-3-benzyloxy-4-benzyloxymethylcyclopentan-1-ol (114826-94-7)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; for 0.666667h; Ambient temperature;

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

upstream raw materials:

2-((1S,3S,4R)-3-Benzyloxy-4-benzyloxymethyl-cyclopentyloxy)-tetrahydro-pyran

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

benzyl bromide

(1S,2R)-2-(benzyloxymethyl)-1-hydroxy-3-cyclopentene

Downstream raw materials:

1-((1R,3S,4R)-3-Benzyloxy-4-benzyloxymethyl-cyclopentyl)-3-benzyloxymethyl-5-methyl-1H-pyrimidine-2,4-dione

1-(3',5'-di-O-benzyl-2'-deoxy-6'-carba-β-D-ribofuranosyl)thymine

(+)-1-<(1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl>-5-<(E)-2-bromovinyl>-1H,3H-pyrimidine-2,4-dione

9-[(1R,3S,4R)-3-benzyloxy-4-(benzyloxymethyl)cyclopentyl]2,4-bis(trifluoromethyl)-9H-pyrido[2,3-b]indole

Refernces

• 1、 Mahler, Miriam,Reichardt, Bastian,Hartjen, Philip,Van Lunzen, Jan,Meier, Chris. "Stereoselective synthesis of D - And L -carbocyclic nucleosides by enzymatically catalyzed kinetic resolution". experimental part. p. 11046 - 11062. Retrieved 2012/10/07.
• 2、 Ludek,Meier. "Synthesis of carbocyclic analogues of thymidine". . p. 683 - 685. Retrieved 2007/10/03.