tert-butyl N-allyl-(1R)-1-{(2R)-2-[(4-methoxybenzyl)oxy]-2-phenylethyl}but-3-enylcarbamate

Base Information

Chemical Name:tert-butyl N-allyl-(1R)-1-{(2R)-2-[(4-methoxybenzyl)oxy]-2-phenylethyl}but-3-enylcarbamate
CAS No.:311772-66-4
Molecular Formula:C₂₈H₃₇NO₄
Molecular Weight:451.606
Hs Code.:

Synonyms:tert-butyl N-allyl-(1R)-1-{(2R)-2-[(4-methoxybenzyl)oxy]-2-phenylethyl}but-3-enylcarbamate

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Chemical Property of tert-butyl N-allyl-(1R)-1-{(2R)-2-[(4-methoxybenzyl)oxy]-2-phenylethyl}but-3-enylcarbamate

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Technology Process of tert-butyl N-allyl-(1R)-1-{(2R)-2-[(4-methoxybenzyl)oxy]-2-phenylethyl}but-3-enylcarbamate

There total 12 articles about tert-butyl N-allyl-(1R)-1-{(2R)-2-[(4-methoxybenzyl)oxy]-2-phenylethyl}but-3-enylcarbamate 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: 91.0%

: 106-95-6
allyl bromide

: 311772-65-3
tert-butyl (1R)-1-{(2R)-2-[(4-methoxybenzyl)oxy]-2-phenylethyl}but-3-enylcarbamate

: 311772-66-4
tert-butyl N-allyl-(1R)-1-{(2R)-2-[(4-methoxybenzyl)oxy]-2-phenylethyl}but-3-enylcarbamate

Guidance literature:: With potassium hexamethylsilazane; In tetrahydrofuran; N,N-dimethyl-formamide;

Reference yield:

: 100-52-7
benzaldehyde

: 311772-66-4
tert-butyl N-allyl-(1R)-1-{(2R)-2-[(4-methoxybenzyl)oxy]-2-phenylethyl}but-3-enylcarbamate

Guidance literature:: Multi-step reaction with 6 steps

1.1: chiral titanium complex / tetrahydrofuran; diethyl ether / 2 h / 0 °C

1.2: tetrahydrofuran; diethyl ether / 3 h / -78 °C

1.3: 2.10 g / t-BuOK / tetrahydrofuran / 4 h / 20 °C

2.1: OsO₄ / tetrahydrofuran; H₂O / 0.08 h / 20 °C

2.2: 2.17 g / NaIO₄ / tetrahydrofuran; H₂O / 2 h

3.1: chiral titanium complex / tetrahydrofuran; diethyl ether / 2 h / 0 °C

3.2: tetrahydrofuran; diethyl ether / 3 h / -78 °C

3.3: 1.62 g / PPh₃; DEAD; DPPA / tetrahydrofuran / 12 h / 20 °C

4.1: 94 percent / LiAlH₄ / diethyl ether / 2 h / 0 - 20 °C

5.1: 85 percent / dioxane / 19 h / 20 °C

6.1: KHMDS / tetrahydrofuran; dimethylformamide; toluene / 0.5 h / 0 °C

6.2: 91 percent / tetrahydrofuran; dimethylformamide; toluene / 2 h / 20 °C

With osmium(VIII) oxide; lithium aluminium tetrahydride; potassium hexamethylsilazane; chiral titanium complex; In tetrahydrofuran; 1,4-dioxane; diethyl ether; water; N,N-dimethyl-formamide; toluene; 3.3: Mitsunobu reaction;
DOI:10.1021/jo010653d

Reference yield:

: 405114-20-7
(3R)-3-[(4-methoxybenzyl)oxy]-3-phenylpropanal

: 311772-66-4
tert-butyl N-allyl-(1R)-1-{(2R)-2-[(4-methoxybenzyl)oxy]-2-phenylethyl}but-3-enylcarbamate

Guidance literature:: Multi-step reaction with 4 steps

1.1: chiral titanium complex / tetrahydrofuran; diethyl ether / 2 h / 0 °C

1.2: tetrahydrofuran; diethyl ether / 3 h / -78 °C

1.3: 1.62 g / PPh₃; DEAD; DPPA / tetrahydrofuran / 12 h / 20 °C

2.1: 94 percent / LiAlH₄ / diethyl ether / 2 h / 0 - 20 °C

3.1: 85 percent / dioxane / 19 h / 20 °C

4.1: KHMDS / tetrahydrofuran; dimethylformamide; toluene / 0.5 h / 0 °C

4.2: 91 percent / tetrahydrofuran; dimethylformamide; toluene / 2 h / 20 °C

With lithium aluminium tetrahydride; potassium hexamethylsilazane; chiral titanium complex; In tetrahydrofuran; 1,4-dioxane; diethyl ether; N,N-dimethyl-formamide; toluene; 1.3: Mitsunobu reaction;
DOI:10.1021/jo010653d