(+)-3-(benzyloxymethoxymethyl)-4-butanolide

Base Information

• Chemical Name: (+)-3-(benzyloxymethoxymethyl)-4-butanolide
• CAS No.: 113681-08-6
• Molecular Formula: C₁₃H₁₆O₄
• Molecular Weight: 236.268
• Mol file: 113681-08-6.mol

Synonyms:(+)-3-(benzyloxymethoxymethyl)-4-butanolide

Chemical Property of (+)-3-(benzyloxymethoxymethyl)-4-butanolide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-3-(benzyloxymethoxymethyl)-4-butanolide

There total 5 articles about (+)-3-(benzyloxymethoxymethyl)-4-butanolide 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: 70.0%

(R)-4-Benzyloxymethoxy-3-hydroxymethyl-butyric acid tert-butyl ester (201804-37-7) → (+)-3-(benzyloxymethoxymethyl)-4-butanolide (113681-08-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 0.333333h;

DOI:10.1016/S0957-4166(97)00560-0

Reference yield:

(S)-4-Acetoxy-3-benzyloxymethoxymethyl-butyric acid tert-butyl ester (201804-36-6) → (+)-3-(benzyloxymethoxymethyl)-4-butanolide (113681-08-6)

Guidance literature:

With lithium hydroxide; 2-chloro-1-methyl-pyridinium iodide; triethylamine; Yield given. Multistep reaction; 1.) THF, H₂O, 2.) CH₂Cl₂, RT, 2 h;

DOI:10.1016/S0957-4166(97)00560-0

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → (+)-3-(benzyloxymethoxymethyl)-4-butanolide (113681-08-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / EtN(iPr)2 / CH₂Cl₂ / 8 h / Ambient temperature

2: 1.) LiOH, 2.) Et₃N, N-methyl 2-chloropyridinium iodide / 1.) THF, H₂O, 2.) CH₂Cl₂, RT, 2 h

With lithium hydroxide; 2-chloro-1-methyl-pyridinium iodide; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1016/S0957-4166(97)00560-0

upstream raw materials:

[(ethoxymethoxy)methyl]benzene

tri-n-butylstannylmethanol

(R)-4-Benzyloxymethoxy-3-hydroxymethyl-butyric acid tert-butyl ester

(S)-4-Acetoxy-3-benzyloxymethoxymethyl-butyric acid tert-butyl ester

Refernces

• 1、 Posner, Gary H.,Weitzberg, Moshe,Jew, Sang-sup. "ASYMMETRIC CONJUGATE ADDITIONS OF AN HYDROXYMETHYL CARBANION EQUIVALENT. SYNTHESIS OF (+)-A FACTOR". . p. 611 - 620. Retrieved 2007/10/02.