(2R,3R,4R)-5-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylpentanal

Base Information

• Chemical Name: (2R,3R,4R)-5-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylpentanal
• CAS No.: 235785-57-6
• Molecular Formula: C₃₁H₄₀O₄Si
• Molecular Weight: 504.742
• Mol file: 235785-57-6.mol

Synonyms:(2R,3R,4R)-5-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylpentanal

Chemical Property of (2R,3R,4R)-5-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylpentanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R)-5-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylpentanal

There total 5 articles about (2R,3R,4R)-5-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylpentanal 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%

(2S,3S,4R)-5-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylpentan-1-ol (1184871-22-4) → (2R,3R,4R)-5-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylpentanal (235785-57-6)

Guidance literature:

With pyridine; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1002/anie.200901608

Reference yield:

(2R,3R,4S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3-[(para-methoxybenzyl)oxy]-5,6-hexanediol (502846-33-5) → (2R,3R,4R)-5-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylpentanal (235785-57-6)

Guidance literature:

With sodium periodate; In tetrahydrofuran; water; for 1h;

DOI:10.1021/jo0267908

Reference yield:

(3R,4S,5S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3-[(para-methoxybenzyl)oxy]-5-hexene (502846-32-4) → (2R,3R,4R)-5-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylpentanal (235785-57-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / OsO₄; N-methylmorpholine N-oxide / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 23 °C

2: NaIO₄ / tetrahydrofuran; H₂O / 1 h

With sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; tert-butyl alcohol;

DOI:10.1021/jo0267908

upstream raw materials:

(2R,3R,4S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3-[(para-methoxybenzyl)oxy]-5,6-hexanediol

(3R,4S,5S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3-[(para-methoxybenzyl)oxy]-5-hexene

O-(4-methoxybenzyl)-trichloroacetimidate

(2S,3S,4R)-5-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylpentan-1-ol

Downstream raw materials:

(2R,3R,4S,5S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-5-hydroxy-3-[(para-methoxybenzyl)oxy]-2,4,6-trimethyloct-7-ene

(2R,3R,4S,5S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-2,4,6-trimethyl-3,5-dihydroxyoct-7-ene

(2R,3S,4S)-6-((2S,2'R,5S,5'S)-5'-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-2,5'-dimethyloctahydro-[2,2'-bifuran]-5-yl)-1-((tert-butyldiphenylsilyl)oxy)-2,4-dimethylhex-5-en-3-ol

(2S,2'R,5'S)-5'-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-5-[(3S,4S,5R,Z)-6-(tert-butyldiphenylsilyloxy)-4-(4-methoxybenzyloxy)-3,5-dimethylhex-1-enyl]-2,5'-dimethyloctahydro-2,2'-bifuran