(S)-4-(benzyloxycarbonylamino)-3-(benzyloxymethoxy)butyric acid

Base Information

• Chemical Name: (S)-4-(benzyloxycarbonylamino)-3-(benzyloxymethoxy)butyric acid
• CAS No.: 1607830-41-0
• Molecular Formula: C₂₀H₂₃NO₆
• Molecular Weight: 373.406
• Mol file: 1607830-41-0.mol

Synonyms:(S)-4-(benzyloxycarbonylamino)-3-(benzyloxymethoxy)butyric acid

Chemical Property of (S)-4-(benzyloxycarbonylamino)-3-(benzyloxymethoxy)butyric acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-(benzyloxycarbonylamino)-3-(benzyloxymethoxy)butyric acid

There total 8 articles about (S)-4-(benzyloxycarbonylamino)-3-(benzyloxymethoxy)butyric acid 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: 63.0%

(S)-3-phenylallyl 4-(penzyloxycarbonylamino)-3-(benzyloxymethoxy)butyrate → (S)-4-(benzyloxycarbonylamino)-3-(benzyloxymethoxy)butyric acid (1607830-41-0)

Guidance literature:

With morpholine; palladium diacetate; triphenylphosphine; In ethanol; for 3h; Inert atmosphere; Reflux;

DOI:10.1002/ejoc.201301374

Reference yield:

(R)-mono(3-phenylallyl) 3-(benzyloxymethoxy)glutarate → (S)-4-(benzyloxycarbonylamino)-3-(benzyloxymethoxy)butyric acid (1607830-41-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: diphenyl phosphoryl azide; triethylamine / toluene / 0.5 h / 20 - 90 °C / Inert atmosphere

1.2: Inert atmosphere; Reflux

2.1: morpholine; triphenylphosphine; palladium diacetate / ethanol / 3 h / Inert atmosphere; Reflux

With morpholine; diphenyl phosphoryl azide; palladium diacetate; triethylamine; triphenylphosphine; In ethanol; toluene;

DOI:10.1002/ejoc.201301374

Reference yield:

3-(benzyloxymethoxy)glutaric acid (1607830-31-8) → (S)-4-(benzyloxycarbonylamino)-3-(benzyloxymethoxy)butyric acid (1607830-41-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: acetic anhydride / 1.5 h / 100 °C / Inert atmosphere

2.1: C₂₇H₃₁N₃O₃S / tert-butyl methyl ether / Inert atmosphere

3.1: diphenyl phosphoryl azide; triethylamine / toluene / 0.5 h / 20 - 90 °C / Inert atmosphere

3.2: Inert atmosphere; Reflux

4.1: morpholine; triphenylphosphine; palladium diacetate / ethanol / 3 h / Inert atmosphere; Reflux

With morpholine; diphenyl phosphoryl azide; C₂₇H₃₁N₃O₃S; palladium diacetate; triethylamine; triphenylphosphine; In ethanol; tert-butyl methyl ether; acetic anhydride; toluene;

DOI:10.1002/ejoc.201301374

upstream raw materials:

3-(benzyloxymethoxy)glutaric acid

3-(benzyloxymethoxy)glutaric anhydride

diethyl 3-(benzyloxymethyloxy)glutarate

Benzyloxymethyl chloride

Refernces

• 1、 Ivic, Trpimir,Dokli, Irena,Rimac, Ana,Hamerak, Zdenko. "Synthesis of GABOB and GABOB-Based Chiral Units Possessing Distinct Protecting Groups". . p. 631 - 638. Retrieved 2015/10/05.