tert-butyl N-{(1S)-3-diazo-1-[(1R)-1-(benzyloxy)ethyl]-2-oxopropyl}carbamate

Base Information

• Chemical Name: tert-butyl N-{(1S)-3-diazo-1-[(1R)-1-(benzyloxy)ethyl]-2-oxopropyl}carbamate
• CAS No.: 210533-59-8
• Molecular Formula: C₁₇H₂₃N₃O₄
• Molecular Weight: 333.387

Synonyms:tert-butyl N-{(1S)-3-diazo-1-[(1R)-1-(benzyloxy)ethyl]-2-oxopropyl}carbamate

Chemical Property of tert-butyl N-{(1S)-3-diazo-1-[(1R)-1-(benzyloxy)ethyl]-2-oxopropyl}carbamate

Chemical Property:

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MSDS Files:

SDS file from LookChem

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Technology Process of tert-butyl N-{(1S)-3-diazo-1-[(1R)-1-(benzyloxy)ethyl]-2-oxopropyl}carbamate

There total 3 articles about tert-butyl N-{(1S)-3-diazo-1-[(1R)-1-(benzyloxy)ethyl]-2-oxopropyl}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: 55.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + N-Boc-O-benzyl-L-threonine (15260-10-3) + chloroformic acid ethyl ester (541-41-3) → tert-butyl N-{(1S)-3-diazo-1-[(1R)-1-(benzyloxy)ethyl]-2-oxopropyl}carbamate (210533-59-8)

Guidance literature:

N-Boc-O-benzyl-L-threonine; chloroformic acid ethyl ester; With triethylamine; In tetrahydrofuran; at -15 ℃; for 0.25h;

diazomethane; In diethyl ether; at 20 ℃; for 3h;

DOI:10.1002/(SICI)1522-2675(20000119)83:1<16::AID-HLCA16>3.0.CO;2-3

Reference yield:

N-Boc-O-benzyl-L-threonine (15260-10-3) → tert-butyl N-{(1S)-3-diazo-1-[(1R)-1-(benzyloxy)ethyl]-2-oxopropyl}carbamate (210533-59-8)

Guidance literature:

Multi-step reaction with 2 steps

1: NMM / tetrahydrofuran / 1 h / -25 °C

2: diethyl ether / 2 h / Ambient temperature

With 4-methyl-morpholine; In tetrahydrofuran; diethyl ether;

DOI:10.1016/S0040-4039(98)00675-3

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + C21H31NO7 (84890-92-6) → tert-butyl N-{(1S)-3-diazo-1-[(1R)-1-(benzyloxy)ethyl]-2-oxopropyl}carbamate (210533-59-8)

Guidance literature:

In diethyl ether; for 2h; Yield given; Ambient temperature;

DOI:10.1016/S0040-4039(98)00675-3

upstream raw materials:

diazomethane

C₂₁H₃₁NO₇

N-Boc-O-benzyl-L-threonine

chloroformic acid ethyl ester

Downstream raw materials:

Boc-β³-HTrp(OBn)-β³-HLys(N^ε-2-Cl-Z)-OMe

Boc-N-Me-β³-HThr(OBn)-β³-HLys(N^ε-2-Cl-Z)-OMe

(3R,4R)-4-(benzyloxy)-3-{[(tert-butoxy)carbonyl](methyl)amino}pentanoic acid

(3R,4R)-4-(benzyloxy)-3-{[(tert-butoxy)carbonyl]amino}pentanoic acid

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