(1S,3S,4R)-1-benzyloxy-4-(3,3-ethylenedioxybutyl)-3-methoxycarbonylcyclopentane

Base Information

• Chemical Name: (1S,3S,4R)-1-benzyloxy-4-(3,3-ethylenedioxybutyl)-3-methoxycarbonylcyclopentane
• CAS No.: 101909-81-3
• Molecular Formula: C₂₀H₂₈O₅
• Molecular Weight: 348.439
• Mol file: 101909-81-3.mol

Synonyms:(1S,3S,4R)-1-benzyloxy-4-(3,3-ethylenedioxybutyl)-3-methoxycarbonylcyclopentane

Chemical Property of (1S,3S,4R)-1-benzyloxy-4-(3,3-ethylenedioxybutyl)-3-methoxycarbonylcyclopentane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S,4R)-1-benzyloxy-4-(3,3-ethylenedioxybutyl)-3-methoxycarbonylcyclopentane

There total 13 articles about (1S,3S,4R)-1-benzyloxy-4-(3,3-ethylenedioxybutyl)-3-methoxycarbonylcyclopentane 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: 94.0%

ethylene glycol (107-21-1) + (1S,3S,4R)-1-benzyloxy-3-methoxycarbonyl-4-(3-oxobutyl)-cyclopentane (101909-78-8) → (1S,3S,4R)-1-benzyloxy-4-(3,3-ethylenedioxybutyl)-3-methoxycarbonylcyclopentane (101909-81-3)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 3h; Heating;

DOI:10.1248/cpb.33.4021

Reference yield: 88.0%

(1S,3S,4R)-1-benzyloxy-4-(3,3-ethylenedioxybutyl)-3-methoxycarbonylcyclopentane (101909-81-3) → (1S,3R,4R)-1-benzyloxy-4-(3,3-ethylenedioxybutyl)-3-methoxycarbonylcyclopentane (101909-81-3)

Guidance literature:

With sodium methylate; In toluene; 1 h, r.t; reflux, 3 h;

DOI:10.1248/cpb.33.4021

Reference yield:

(3S,4R)-4-(3-hydroxybutyl)-3-hydroxymethylcyclopentanone (101909-74-4) → (1S,3S,4R)-1-benzyloxy-4-(3,3-ethylenedioxybutyl)-3-methoxycarbonylcyclopentane (101909-81-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / p-toluenesulfonic acid / CH₂Cl₂ / 2 h / Ambient temperature

2: 91 percent / NaBH₄ / methanol / 1 h

3: 1.) sodium methylsulfinylmethide / 1.) DMSO, r.t. 1 h; 2.) DMSO, 6 h, r.t.

4: 1.) Jones reagent / 1.) acetone, < 5 degC, 1.5 h

5: 94 percent / p-toluenesulfonic acid / benzene / 3 h / Heating

With sodium tetrahydroborate; jones reagent; dimsylsodium; toluene-4-sulfonic acid; In methanol; dichloromethane; benzene;

DOI:10.1248/cpb.33.4021

upstream raw materials:

ethylene glycol

(1S,3S,4R)-1-benzyloxy-3-methoxycarbonyl-4-(3-oxobutyl)-cyclopentane

(3S,4R)-4-(3-hydroxybutyl)-3-hydroxymethylcyclopentanone

(1S,3S,4R)-4-<3-(tetrahydropyran-2-yl)oxybutyl>-3-(tetrahydropyran-2-yl)oxymethyl-1-cyclopentanol

Downstream raw materials:

(1S,3R,4R)-1-benzyloxy-3-methoxycarbonyl-4-(3-oxobutyl)-cyclopentane

(1S,3R,4R)-4-(2-acetoxyethyl)-1-benzyloxy-3-methoxycarbonylcyclopentane