(R)-tert-butyl 1-(benzyloxymethyl)-4,6-dihydroxy-3-oxoisoindoline-2-carboxylate

Base Information

• Chemical Name: (R)-tert-butyl 1-(benzyloxymethyl)-4,6-dihydroxy-3-oxoisoindoline-2-carboxylate
• CAS No.: 1313226-84-4
• Molecular Formula: C₂₁H₂₃NO₆
• Molecular Weight: 385.417
• Mol file: 1313226-84-4.mol

Synonyms:(R)-tert-butyl 1-(benzyloxymethyl)-4,6-dihydroxy-3-oxoisoindoline-2-carboxylate

Chemical Property of (R)-tert-butyl 1-(benzyloxymethyl)-4,6-dihydroxy-3-oxoisoindoline-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-tert-butyl 1-(benzyloxymethyl)-4,6-dihydroxy-3-oxoisoindoline-2-carboxylate

There total 4 articles about (R)-tert-butyl 1-(benzyloxymethyl)-4,6-dihydroxy-3-oxoisoindoline-2-carboxylate 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: 88.0%

(S)-tert-butyl 2-(benzyloxy)-1-(7-hydroxy-2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)ethyl carbamate (1313226-72-0) → (R)-tert-butyl 1-(benzyloxymethyl)-4,6-dihydroxy-3-oxoisoindoline-2-carboxylate (1313226-84-4)

Guidance literature:

With caesium carbonate; In methanol; at 60 ℃; for 18h; Inert atmosphere; Sealed tube;

DOI:10.1021/jo2009356

Reference yield:

(S)-tert-butyl 3-(benzyloxy)-1-(1H-imidazol-1-yl)-1-oxopropan-2-ylcarbamate (1313226-62-8) → (R)-tert-butyl 1-(benzyloxymethyl)-4,6-dihydroxy-3-oxoisoindoline-2-carboxylate (1313226-84-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.67 h / -78 °C / Inert atmosphere

1.2: -78 - -30 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 16 h / 20 °C / Inert atmosphere

3.1: caesium carbonate / methanol / 18 h / 60 °C / Inert atmosphere; Sealed tube

With caesium carbonate; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane;

DOI:10.1021/jo2009356

Reference yield:

C24H31NO8 → (R)-tert-butyl 1-(benzyloxymethyl)-4,6-dihydroxy-3-oxoisoindoline-2-carboxylate (1313226-84-4)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 16 h / 20 °C / Inert atmosphere

2: caesium carbonate / methanol / 18 h / 60 °C / Inert atmosphere; Sealed tube

With caesium carbonate; triethylamine; In methanol; dichloromethane;

DOI:10.1021/jo2009356

upstream raw materials:

(S)-tert-butyl 3-(benzyloxy)-1-(1H-imidazol-1-yl)-1-oxopropan-2-ylcarbamate

(S)-tert-butyl 2-(benzyloxy)-1-(7-hydroxy-2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)ethyl carbamate

BOC-O-benzyl-L-serine