(R)-tert-butyl (4-(benzyloxy)-1-iodonaphthalen-2-yl)(oxiran-2-ylmethyl)carbamate

Base Information

• Chemical Name: (R)-tert-butyl (4-(benzyloxy)-1-iodonaphthalen-2-yl)(oxiran-2-ylmethyl)carbamate
• CAS No.: 1116653-76-9
• Molecular Formula: C₂₅H₂₆INO₄
• Molecular Weight: 531.39
• Mol file: 1116653-76-9.mol

Synonyms:(R)-tert-butyl (4-(benzyloxy)-1-iodonaphthalen-2-yl)(oxiran-2-ylmethyl)carbamate

Chemical Property of (R)-tert-butyl (4-(benzyloxy)-1-iodonaphthalen-2-yl)(oxiran-2-ylmethyl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-tert-butyl (4-(benzyloxy)-1-iodonaphthalen-2-yl)(oxiran-2-ylmethyl)carbamate

There total 10 articles about (R)-tert-butyl (4-(benzyloxy)-1-iodonaphthalen-2-yl)(oxiran-2-ylmethyl)carbamate 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: 95.0%

(2s)-(+)-glycidyl 3-nitrobenzenesulfonate (115314-14-2) + tert-butyl (4-(benzyloxy)-1-iodonaphthalen-2-yl)carbamate (161646-53-3) → (R)-tert-butyl (4-(benzyloxy)-1-iodonaphthalen-2-yl)(oxiran-2-ylmethyl)carbamate (1116653-76-9)

Guidance literature:

tert-butyl-(4-(benzyloxy)-1-iodonaphthalen-2-yl)carbamate; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 0.5h;

(2s)-(+)-glycidyl 3-nitrobenzenesulfonate; In N,N-dimethyl-formamide; mineral oil; for 3h;

Reference yield: 88.0%

[(2S)-2-methyloxiran-2-yl]methyl 4-nitrobenzene-1-sulfonate (683276-63-3) + tert-butyl (4-(benzyloxy)-1-iodonaphthalen-2-yl)carbamate (161646-53-3) → (R)-tert-butyl (4-(benzyloxy)-1-iodonaphthalen-2-yl)(oxiran-2-ylmethyl)carbamate (1116653-76-9)

Guidance literature:

tert-butyl-(4-(benzyloxy)-1-iodonaphthalen-2-yl)carbamate; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.0833333h;

[(2S)-2-methyloxiran-2-yl]methyl 4-nitrobenzene-1-sulfonate; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 2.5h;

DOI:10.1021/jo102136w

Reference yield:

N-(tert-butyloxycarbonyl)-4-(benzyloxy)-2-naphthylamine (122745-36-2) → (R)-tert-butyl (4-(benzyloxy)-1-iodonaphthalen-2-yl)(oxiran-2-ylmethyl)carbamate (1116653-76-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: toluene-4-sulfonic acid / tetrahydrofuran / 0.17 h / -20 °C / Inert atmosphere

1.2: 4 h / -20 - 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C / Inert atmosphere

2.2: 12.5 h / 0 - 20 °C

With sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil;

upstream raw materials:

[(2S)-2-methyloxiran-2-yl]methyl 4-nitrobenzene-1-sulfonate

tert-butyl (4-(benzyloxy)-1-iodonaphthalen-2-yl)carbamate

di-tert-butyl dicarbonate

(2s)-(+)-glycidyl 3-nitrobenzenesulfonate

Downstream raw materials:

tert-butyl (1S)-1-(chloromethyl)-5-hydroxy-1,2-dihydro-3H-benzo[e]indole-3-carboxylate

(+)-(1S)-5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole

5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(chloromethyl)-1,2-dihydro-3H-benzindole