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

Base Information

• Chemical Name: (2S,3S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-methyl-pentanal
• CAS No.: 148933-81-7
• Molecular Formula: C₂₀H₃₄O₄Si
• Molecular Weight: 366.573
• Mol file: 148933-81-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (2S,3S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-methyl-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: 89.0%

C22H40O5Si (1082395-57-0) → (2S,3S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-methyl-pentanal (148933-81-7)

Guidance literature:

With sodium periodate; In methanol; at 0 - 20 ℃; pH=7; aq. buffer;

DOI:10.1016/j.tet.2010.01.083

Reference yield: 89.0%

tert-Butyl-[(3S,4R)-3-(4-methoxy-benzyloxy)-4-methyl-hex-5-enyloxy]-dimethyl-silane (148933-64-6) → (2S,3S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-methyl-pentanal (148933-81-7)

Guidance literature:

tert-Butyl-[(3S,4R)-3-(4-methoxy-benzyloxy)-4-methyl-hex-5-enyloxy]-dimethyl-silane; With ozone;

With triphenylphosphine; In dichloromethane; Further stages.;

DOI:10.1016/j.bmcl.2007.02.031

Reference yield:

(3S,4R)-1-[(tert-butyldimethylsilyl)oxy]-4-methylhex-5-en-3-ol (168777-81-9) → (2S,3S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-methyl-pentanal (148933-81-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 87 percent / Sc(OTf)3 / tetrahydrofuran

2.1: O₃

2.2: 89 percent / PPh₃ / CH₂Cl₂

With ozone; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran;

DOI:10.1016/j.bmcl.2007.02.031

upstream raw materials:

tert-Butyl-[(3S,4R)-3-(4-methoxy-benzyloxy)-4-methyl-hex-5-enyloxy]-dimethyl-silane

p-methoxybenzyl trichloroacetate

(3S,4R)-1-[(tert-butyldimethylsilyl)oxy]-4-methylhex-5-en-3-ol

3-(tert-butyldimethylsilanyloxy)propionaldehyde

Downstream raw materials:

tert-Butyl-[(3S,4R)-6,6-dibromo-3-(4-methoxy-benzyloxy)-4-methyl-hex-5-enyloxy]-dimethyl-silane

C₁₅H₂₁O₃I

C₁₅H₁₉O₃I

C₁₅H₁₉O₄I