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

Base Information

• Chemical Name: (1S,3S,4R)-1-benzyloxy-3-methoxycarbonyl-4-(3-oxobutyl)-cyclopentane
• CAS No.: 101909-78-8
• Molecular Formula: C₁₈H₂₄O₄
• Molecular Weight: 304.386
• Mol file: 101909-78-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about (1S,3S,4R)-1-benzyloxy-3-methoxycarbonyl-4-(3-oxobutyl)-cyclopentane 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:

(3S,4R)-4-(3-hydroxybutyl)-3-hydroxymethylcyclopentanone (101909-74-4) → (1S,3S,4R)-1-benzyloxy-3-methoxycarbonyl-4-(3-oxobutyl)-cyclopentane (101909-78-8)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1248/cpb.33.4021

Reference yield:

Benzoic acid (1S,2R)-2-(3-hydroxy-butyl)-4-oxo-cyclopentylmethyl ester (101909-73-3,101978-31-8) → (1S,3S,4R)-1-benzyloxy-3-methoxycarbonyl-4-(3-oxobutyl)-cyclopentane (101909-78-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / K₂CO₃ / methanol / 3 h / Ambient temperature

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

3: 91 percent / NaBH₄ / methanol / 1 h

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

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

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

DOI:10.1248/cpb.33.4021

Reference yield:

(3S,4R)-4-<3-(tetrahydropyran-2-yl)oxybutyl>-3-(tetrahydropyran-2-yl)oxymethylcyclopentanone (101909-75-5) → (1S,3S,4R)-1-benzyloxy-3-methoxycarbonyl-4-(3-oxobutyl)-cyclopentane (101909-78-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / NaBH₄ / methanol / 1 h

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

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

With sodium tetrahydroborate; jones reagent; dimsylsodium; In methanol;

DOI:10.1248/cpb.33.4021

upstream raw materials:

diazomethane

(1S,3S,4R)-1-benzyloxy-4-<3-(tetrahydropyran-2-yl)oxybutyl>-3-(tetrahydropyran-2-yl)oxymethylcyclopentane

(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-4-(3,3-ethylenedioxybutyl)-3-methoxycarbonylcyclopentane

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

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

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