(2S,5R)-2-(carboxymethyl)-5-(1-benzyloxypropyl)tetrahydrofuran

Base Information

• Chemical Name: (2S,5R)-2-(carboxymethyl)-5-(1-benzyloxypropyl)tetrahydrofuran
• CAS No.: 313963-24-5
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.322
• Mol file: 313963-24-5.mol

Synonyms:(2S,5R)-2-(carboxymethyl)-5-(1-benzyloxypropyl)tetrahydrofuran

Chemical Property of (2S,5R)-2-(carboxymethyl)-5-(1-benzyloxypropyl)tetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R)-2-(carboxymethyl)-5-(1-benzyloxypropyl)tetrahydrofuran

There total 8 articles about (2S,5R)-2-(carboxymethyl)-5-(1-benzyloxypropyl)tetrahydrofuran 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:

[(2S,5R)-5-(3-Benzyloxy-propyl)-tetrahydro-furan-2-yl]-methanol (313963-34-7) → (2S,5R)-2-(carboxymethyl)-5-(1-benzyloxypropyl)tetrahydrofuran (313963-24-5)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 0 ℃;

DOI:10.1002/1521-3773(20001016)39:20<3622::AID-ANIE3622>3.0.CO;2-H

Reference yield:

(2S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(1-benzyloxyprop-2-ynyl)tetrahydrofuran (313963-33-6) → (2S,5R)-2-(carboxymethyl)-5-(1-benzyloxypropyl)tetrahydrofuran (313963-24-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

2: 70 percent / H₂ / Raney nickel / ethanol / 0.5 h / 20 °C

3: DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 0.5 h / -78 - 0 °C

With oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; nickel; In tetrahydrofuran; ethanol; dichloromethane; 3: Swern oxidation;

DOI:10.1039/b316858a

Reference yield:

(2S,5S)-2-(hydroxymethyl)-5-(1-benzyloxyprop-2-ynyl)tetrahydrofuran (443303-88-6) → (2S,5R)-2-(carboxymethyl)-5-(1-benzyloxypropyl)tetrahydrofuran (313963-24-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / H₂ / Raney nickel / ethanol / 0.5 h / 20 °C

2: DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 0.5 h / -78 - 0 °C

With oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; nickel; In ethanol; dichloromethane; 2: Swern oxidation;

DOI:10.1039/b316858a

upstream raw materials:

[(2S,5R)-5-(3-Benzyloxy-propyl)-tetrahydro-furan-2-yl]-methanol

benzyl bromide

(2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol

(2S,5S)-2-(hydroxymethyl)-5-(1-benzyloxyprop-2-ynyl)tetrahydrofuran

Downstream raw materials:

(12R,15S,16R/S,19R,20S,34R,35R)-34,35-dimethoxy-34,35-dimethyl-19-(12-(9-benzyloxypropyl)-15-(16-hydroxyprop-17-ynyl)tetrahydrofuran)-20-dodecanyl-[33,36]-dioxane

(12R,15S,16S,19R,20S,34R,35R)-34,35-dimethoxy-34,35-dimethyl-19-(12-(9-benzyloxypropyl)-15-(16-tert-butyldimethylsilyloxypropyl)tetrahydrofuran)-20-dodecanyl-[33,36]-dioxane

(12R,15S,16S,19R,20S,34R,35R)-34,35-dimethoxy-34,35-dimethyl-19-(12-(9-benzyloxypropyl)-15-(16-hydroxypropyl)tetrahydrofuran)-20-dodecanyl-[33,36]-dioxane

(12R,15S,16R/S,19R,20S,34R,35R)-34,35-dimethoxy-34,35-dimethyl-19-(12-(9-benzyloxypropyl)-15-(16-hydroxypropyl)tetrahydrofuran)-20-dodecanyl-[33,36]-dioxane