(2S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentanal

Base Information

• Chemical Name: (2S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentanal
• CAS No.: 172269-21-5
• Molecular Formula: C₂₁H₃₆O₄Si
• Molecular Weight: 380.6
• Mol file: 172269-21-5.mol

Synonyms:(2S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentanal

Chemical Property of (2S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentanal

There total 8 articles about (2S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentanal 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: 92.0%

(2S,2R,4R)-3-[(tert-butyldimethylsilyl)oxy]-N-methoxy-5-[(4-methoxybenzyl)oxy]-N,2,4-trimethylpentanamide (172269-40-8) → (2S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentanal (172269-21-5)

Guidance literature:

With diisbutylaluminum hydride; In tetrahydrofuran; at -78 - 0 ℃;

DOI:10.1016/j.tetlet.2007.08.087

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (2S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentanal (172269-21-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / 2,6-lutidine / CH₂Cl₂

2: 88 percent / DIBAL / tetrahydrofuran

With 2,6-dimethylpyridine; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00153a030

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (2S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentanal (172269-21-5)

Guidance literature:

Multi-step reaction with 7 steps

1: PPTS / CH₂Cl₂; cyclohexane

2: LiAlH₄ / tetrahydrofuran

3: (COCl)2, DMSO

4: n-Bu₂BOTf, Et₃N / CH₂Cl₂

5: 89 percent / AlMe₃ / tetrahydrofuran

6: 100 percent / 2,6-lutidine / CH₂Cl₂

7: 88 percent / DIBAL / tetrahydrofuran

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; cyclohexane;

DOI:10.1021/ja00153a030

upstream raw materials:

(2S,2R,4R)-3-[(tert-butyldimethylsilyl)oxy]-N-methoxy-5-[(4-methoxybenzyl)oxy]-N,2,4-trimethylpentanamide

t-butyldimethylsiyl triflate

O-(4-methoxybenzyl)-trichloroacetimidate

(2S)-3-(4-methoxybenzyloxy)-2-methyl-1-propanol

Downstream raw materials:

(2R,4R,5R)-4-[(Z)-(1S,2S,3R,7R,8S,9S)-2,8-Bis-(tert-butyl-dimethyl-silanyloxy)-10-iodo-1,3,5,7,9-pentamethyl-dec-5-enyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

(Z)-(2R,3S,4R,8R,9S,10S)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-[(2R,4R,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4,6,8-tetramethyl-undec-5-en-1-ol

(2R,4R,5R)-4-[(Z)-(1S,2S,3R,7R,8S,9R)-2,8-Bis-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-1,3,5,7,9-pentamethyl-dec-5-enyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

C₆₃H₁₂₂O₈SSi₄