(1S,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-but-3-enylamine

Base Information

• Chemical Name: (1S,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-but-3-enylamine
• CAS No.: 761407-89-0
• Molecular Formula: C₂₉H₃₇NO₃Si
• Molecular Weight: 475.703
• Mol file: 761407-89-0.mol

Synonyms:(1S,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-but-3-enylamine

Chemical Property of (1S,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-but-3-enylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-but-3-enylamine

There total 10 articles about (1S,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-but-3-enylamine 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: 83.0%

[(2S,3R)-2-Azido-3-(4-methoxy-benzyloxy)-pent-4-enyloxy]-tert-butyl-diphenyl-silane (761407-86-7) → (1S,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-but-3-enylamine (761407-89-0)

Guidance literature:

With ammonium chloride; zinc; In methanol; at 20 ℃; for 2h;

DOI:10.1021/ol049183a

Reference yield:

Benzoic acid (2S,3S)-3-azido-4-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-butyl ester (761408-02-0) → (1S,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-but-3-enylamine (761407-89-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 75 percent / NaHCO₃ / La(OTf)3 / toluene / 2 h

2.1: 81 percent / NaOMe / methanol / 1 h / 20 °C

3.1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

3.2: 92 percent / NaOH / CH₂Cl₂; H₂O; diethyl ether / 20 °C

4.1: 76 percent / BuLi / tetrahydrofuran / -78 - 20 °C

5.1: 83 percent / NH₄Cl; Zn / methanol / 2 h / 20 °C

With n-butyllithium; sodium methylate; sodium hydrogencarbonate; ammonium chloride; Dess-Martin periodane; zinc; lanthanum(lll) triflate; In tetrahydrofuran; methanol; dichloromethane; toluene; 4.1: Wittig methylenation;

DOI:10.1021/ol049183a

Reference yield:

(2S,3S)-3-Azido-4-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-butyraldehyde (761407-84-5) → (1S,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-but-3-enylamine (761407-89-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / BuLi / tetrahydrofuran / -78 - 20 °C

2: 83 percent / NH₄Cl; Zn / methanol / 2 h / 20 °C

With n-butyllithium; ammonium chloride; zinc; In tetrahydrofuran; methanol; 1: Wittig methylenation;

DOI:10.1021/ol049183a

upstream raw materials:

[(2S,3R)-2-Azido-3-(4-methoxy-benzyloxy)-pent-4-enyloxy]-tert-butyl-diphenyl-silane

Methanesulfonic acid (1R,2R)-2-hydroxy-1-hydroxymethyl-but-3-enyl ester

Methanesulfonic acid (1R,2R)-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-but-3-enyl ester

O-(4-methoxybenzyl)-trichloroacetimidate

Downstream raw materials:

Hexadecanoic acid [(E)-(1S,2R)-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-heptadec-3-enyl]-amide

[1-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-heptadec-3-enyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

1-OTBDPS ceramide

(2S,3R,4E)-2-(hexadecanoylamido)-4-octadecene-1,3-diol