(1S.2R)-1-Benzyloxy-2-(benzyloxymethyl)-3-cyclopentene

Base Information

• Chemical Name: (1S.2R)-1-Benzyloxy-2-(benzyloxymethyl)-3-cyclopentene
• CAS No.: 191480-69-0
• Molecular Formula: C20H22 O2
• Molecular Weight: 294.393
• DSSTox Substance ID: DTXSID901153740
• Nikkaji Number: J1.245.928I
• Mol file: 191480-69-0.mol

Synonyms:191480-69-0;[(1R,5S)-5-phenylmethoxycyclopent-2-en-1-yl]methoxymethylbenzene;({[(1S,2R)-2-[(benzyloxy)methyl]cyclopent-3-en-1-yl]oxy}methyl)benzene;(1S.2R)-1-Benzyloxy-2-(benzyloxymethyl)-3-cyclopentene;SCHEMBL22241751;RCWWCVLXNCRBOO-UXHICEINSA-N;DTXSID901153740;(3R)-3alpha-(Benzyloxymethyl)-4beta-(benzyloxy)-1-cyclopentene;[[[(1R,5S)-5-(Phenylmethoxy)-2-cyclopenten-1-yl]methoxy]methyl]benzene

Chemical Property of (1S.2R)-1-Benzyloxy-2-(benzyloxymethyl)-3-cyclopentene

Chemical Property:

• PSA: 18.46000
• LogP: 4.36470
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 294.161979940
• Heavy Atom Count: 22
• Complexity: 327

Purity/Quality:

99%min ^*data from raw suppliers

(1S,2R)-1-BENZYLOXY-2-(BENZYLOXYMETHYL)-3-CYCLOPENTENE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=CC(C1OCC2=CC=CC=C2)COCC3=CC=CC=C3
• Isomeric SMILES: C1C=C[C@@H]([C@H]1OCC2=CC=CC=C2)COCC3=CC=CC=C3

Technology Process of (1S.2R)-1-Benzyloxy-2-(benzyloxymethyl)-3-cyclopentene

There total 10 articles about (1S.2R)-1-Benzyloxy-2-(benzyloxymethyl)-3-cyclopentene 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: 97.4%

benzyl bromide (100-39-0) + (1S,2R)-2-(benzyloxymethyl)-1-hydroxy-3-cyclopentene (110567-21-0) → (3R,4S)-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]cyclopent-1-ene (191480-69-0)

Guidance literature:

(1S,2R)-2-(benzyloxymethyl)-1-hydroxy-3-cyclopentene; With sodium t-butanolate; In tetrahydrofuran; at 20 ℃; for 0.416667h; Inert atmosphere;

benzyl bromide; In tetrahydrofuran; at -5 ℃; for 0.583333h; Temperature; Inert atmosphere;

Reference yield: 97.4%

C13H18O2 + benzyl bromide (100-39-0) → (3R,4S)-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]cyclopent-1-ene (191480-69-0)

Guidance literature:

C₁₃H₁₈O₂; With sodium t-butanolate; In tetrahydrofuran; at 20 ℃; for 0.416667h; Inert atmosphere;

benzyl bromide; In tetrahydrofuran; at -5 ℃; for 0.583333h; Temperature; Inert atmosphere;

Reference yield: 94.0%

benzyl bromide (100-39-0) + (1S,2R)-2-(hydroxymethyl)cyclopent-3-enol (850224-36-1) → (3R,4S)-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]cyclopent-1-ene (191480-69-0)

Guidance literature:

(1S,2R)-2-(hydroxymethyl)cyclopent-3-enol; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 1h;

benzyl bromide; In tetrahydrofuran; mineral oil; for 3h; Reflux;

DOI:10.1016/j.bmc.2014.12.039

upstream raw materials:

benzyl bromide

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

Benzyloxymethyl chloride

5-(benzyloxymethyl)cyclopentadiene

Downstream raw materials:

(3S,4R)-3-(benzyloxy)-4-(benzyloxymethyl)cyclopentanone

C₂₄H₃₁NO₃S

C₃₀H₃₇NO₃S

C₃₀H₃₇NO₃S

Refernces

• 1、 -. "METTL3 MODULATORS". Page/Page column 63. . Retrieved 2021/04/30.
• 2、 -. "PCSK9 INHIBITORS AND METHODS OF USE THEREOF". Page/Page column 146-148. . Retrieved 2020/07/31.