(S)-tert-butyl 2-(bis(benzyloxy)phosphoryl)-2-diazo-1-phenylethylcarbamate

Base Information

Chemical Name:(S)-tert-butyl 2-(bis(benzyloxy)phosphoryl)-2-diazo-1-phenylethylcarbamate
CAS No.:1367878-26-9
Molecular Formula:C₂₇H₃₀N₃O₅P
Molecular Weight:507.526
Hs Code.:

Synonyms:(S)-tert-butyl 2-(bis(benzyloxy)phosphoryl)-2-diazo-1-phenylethylcarbamate

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Chemical Property of (S)-tert-butyl 2-(bis(benzyloxy)phosphoryl)-2-diazo-1-phenylethylcarbamate

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Technology Process of (S)-tert-butyl 2-(bis(benzyloxy)phosphoryl)-2-diazo-1-phenylethylcarbamate

There total 5 articles about (S)-tert-butyl 2-(bis(benzyloxy)phosphoryl)-2-diazo-1-phenylethylcarbamate 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: 94.0%

: 36958-20-0
dibenzyl (diazomethyl)phosphonate

: 150884-50-7
benzaldehyde N-boc imine

: 1367878-26-9
(S)-tert-butyl 2-(bis(benzyloxy)phosphoryl)-2-diazo-1-phenylethylcarbamate

Guidance literature:: With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; In toluene; at -40 ℃; for 1.66667h; optical yield given as %ee; enantioselective reaction; Molecular sieve; Inert atmosphere;
DOI:10.1021/ol300664d

Reference yield:

: O-dibenzyl-aminomethylphosphonate

: 1367878-26-9
(S)-tert-butyl 2-(bis(benzyloxy)phosphoryl)-2-diazo-1-phenylethylcarbamate

Guidance literature:: Multi-step reaction with 2 steps

1: acetic acid; sodium nitrite / water / 0.17 h / 0 °C

2: (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid / toluene / 1.67 h / -40 °C / Molecular sieve; Inert atmosphere

With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; acetic acid; sodium nitrite; In water; toluene; 2: asymmetric Mannich reaction;
DOI:10.1021/ol300664d

Reference yield:

: 100-51-6,185532-71-2
benzyl alcohol

: 1367878-26-9
(S)-tert-butyl 2-(bis(benzyloxy)phosphoryl)-2-diazo-1-phenylethylcarbamate

Guidance literature:: Multi-step reaction with 5 steps

1.1: N,N-dimethyl-aniline; phosphorus trichloride / toluene / 1 h / 0 - 20 °C

1.2: 0.5 h / 20 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / -15 °C

2.2: 16.17 h / -15 - 20 °C

3.1: hydrazine / ethanol / 12 h / Reflux

4.1: acetic acid; sodium nitrite / water / 0.17 h / 0 °C

5.1: (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid / toluene / 1.67 h / -40 °C / Molecular sieve; Inert atmosphere

With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; sodium hydride; acetic acid; N,N-dimethyl-aniline; hydrazine; sodium nitrite; phosphorus trichloride; In tetrahydrofuran; ethanol; water; toluene; mineral oil; 5.1: asymmetric Mannich reaction;
DOI:10.1021/ol300664d