(2R,3R)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanal

Base Information

• Chemical Name: (2R,3R)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanal
• CAS No.: 697751-93-2
• Molecular Formula: C₂₁H₂₈O₂Si
• Molecular Weight: 340.538
• Mol file: 697751-93-2.mol

Synonyms:(2R,3R)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanal

Chemical Property of (2R,3R)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanal

There total 5 articles about (2R,3R)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanal 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%

(2R,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-butyric acid ethyl ester (697751-89-6) → (2R,3R)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanal (697751-93-2)

Guidance literature:

With diisobutylaluminium hydride; In diethyl ether; at -78 ℃;

DOI:10.1039/b401076k

Reference yield:

(2R,3R)-methyl 3-(tert-butyldiphenylsilyloxy)-2-methylbutanoate (1379802-89-7) → (2R,3R)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanal (697751-93-2)

Guidance literature:

With diisobutylaluminium hydride; In hexane; toluene; at -78 ℃; Inert atmosphere;

DOI:10.1002/chem.201102797

Reference yield:

ethyl anti-(2R,3R)-2-methyl-3-hydroxybutanoate (27372-03-8,51898-35-2,51898-36-3,63647-69-8,78088-27-4,78088-28-5,86853-34-1,92282-67-2,86853-33-0) → (2R,3R)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanal (697751-93-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / imidazole / tetrahydrofuran

2: 94 percent / DIBAL-H / diethyl ether / -78 °C

With 1H-imidazole; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether;

DOI:10.1039/b401076k

upstream raw materials:

(2R,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-butyric acid ethyl ester

ethyl anti-(2R,3R)-2-methyl-3-hydroxybutanoate

(2R,3R)-methyl 3-(tert-butyldiphenylsilyloxy)-2-methylbutanoate

methyl 2R,3R-nilate

Downstream raw materials:

(R)-1-((4S,5R)-3-((2S,3R)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-4-methyl-4,5-dihydroisoxazol-5-yl)-2-(trityloxy)ethanol

Benzoic acid (3E,15E)-(1R,2S,5S,6R,10S,12R,14S)-14-(tert-butyl-dimethyl-silanyloxy)-16-ethyl-5-(4-methoxy-benzyloxy)-1,2,6,10,12-pentamethyl-7-oxo-octadeca-3,15,17-trienyl ester

Acetic acid (3E,15E)-(1R,2S,5S,6R,10S,12R,14S)-14-(tert-butyl-dimethyl-silanyloxy)-16-ethyl-5-(4-methoxy-benzyloxy)-1,2,6,10,12-pentamethyl-7-oxo-octadeca-3,15,17-trienyl ester

(E)-(2R,3S,6S,7R)-7-(tert-Butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,6-dimethyl-oct-4-enoic acid methyl ester

Refernces

• 1、 Jamieson, Andrew G.,Sutherland, Andrew,Willis, Christine L.. "The first enantioselective synthesis of the amino acid, (2S,3S,4R)-γ-hydroxyisoleucine using a palladium(ii) catalysed 3,3-sigmatropic rearrangement". . p. 808 - 809. Retrieved 2007/10/03.