(2R)-methyl 2-{2-[(2R,3E)-5-(benzyloxy)pent-3-en-2-yl]-4-(methoxymethoxy)-5-methylphenoxy}-4-(tert-butyldiphenylsilyloxy)butanoate

Base Information

• Chemical Name: (2R)-methyl 2-{2-[(2R,3E)-5-(benzyloxy)pent-3-en-2-yl]-4-(methoxymethoxy)-5-methylphenoxy}-4-(tert-butyldiphenylsilyloxy)butanoate
• CAS No.: 1528746-70-4
• Molecular Formula: C₄₂H₅₂O₇Si
• Molecular Weight: 696.956
• Mol file: 1528746-70-4.mol

Synonyms:(2R)-methyl 2-{2-[(2R,3E)-5-(benzyloxy)pent-3-en-2-yl]-4-(methoxymethoxy)-5-methylphenoxy}-4-(tert-butyldiphenylsilyloxy)butanoate

Chemical Property of (2R)-methyl 2-{2-[(2R,3E)-5-(benzyloxy)pent-3-en-2-yl]-4-(methoxymethoxy)-5-methylphenoxy}-4-(tert-butyldiphenylsilyloxy)butanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-methyl 2-{2-[(2R,3E)-5-(benzyloxy)pent-3-en-2-yl]-4-(methoxymethoxy)-5-methylphenoxy}-4-(tert-butyldiphenylsilyloxy)butanoate

There total 2 articles about (2R)-methyl 2-{2-[(2R,3E)-5-(benzyloxy)pent-3-en-2-yl]-4-(methoxymethoxy)-5-methylphenoxy}-4-(tert-butyldiphenylsilyloxy)butanoate 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: 100.0%

(2R,3E)-2-[5-(benzyloxy)pent-3-en-2-yl]-4-(methoxymethoxy)-5-methylphenol (1313708-38-1) + (2S)-methyl 2-(trifluoromethylsulfonyloxy)-4-(tert-butyldiphenylsilyloxy)butanoate (1528746-69-1) → (2R)-methyl 2-{2-[(2R,3E)-5-(benzyloxy)pent-3-en-2-yl]-4-(methoxymethoxy)-5-methylphenoxy}-4-(tert-butyldiphenylsilyloxy)butanoate (1528746-70-4)

Guidance literature:

With potassium carbonate; In acetonitrile; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1016/j.tet.2013.11.070

Reference yield:

Methyl (2S)-4-<(tert-butyldiphenylsilyl)oxy>-2-hydroxybutyrate (153011-60-0) → (2R)-methyl 2-{2-[(2R,3E)-5-(benzyloxy)pent-3-en-2-yl]-4-(methoxymethoxy)-5-methylphenoxy}-4-(tert-butyldiphenylsilyloxy)butanoate (1528746-70-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,6-dimethylpyridine / dichloromethane / 0.33 h / -20 °C / Inert atmosphere

2: potassium carbonate / acetonitrile / 4 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; potassium carbonate; In dichloromethane; acetonitrile;

DOI:10.1016/j.tet.2013.11.070

Reference yield: 84.0%

(2R)-methyl 2-{2-[(2R,3E)-5-(benzyloxy)pent-3-en-2-yl]-4-(methoxymethoxy)-5-methylphenoxy}-4-(tert-butyldiphenylsilyloxy)butanoate (1528746-70-4) + methylmagnesium bromide (75-16-1) → (3R)-3-[2-(2R,3E)-5-benzyloxypent-3-en-2-yl-4-methoxymethoxy-5-methylphenoxy]-5-(tert-butyldiphenylsilyloxy)-2-methylpentan-2-ol (1528746-72-6)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tet.2013.11.070

upstream raw materials:

(2R,3E)-2-[5-(benzyloxy)pent-3-en-2-yl]-4-(methoxymethoxy)-5-methylphenol

(2S)-methyl 2-(trifluoromethylsulfonyloxy)-4-(tert-butyldiphenylsilyloxy)butanoate

Methyl (2S)-4-<(tert-butyldiphenylsilyl)oxy>-2-hydroxybutyrate

Downstream raw materials:

(3R)-3-{2-[(2R,3E)-5-(benzyloxy)pent-3-en-2-yl]-4-(methoxymethoxy)-5-methylphenoxy}-4-methylpentane-1,4-diol

C₃₃H₄₁NO₇Se

(3R)-3-{2-[(2R,3E)-5-(benzyloxy)pent-3-en-2-yl]-4-(methoxymethoxy)-5-methylphenoxy}-2-methylpent-4-en-2-ol

6-[(2R,3E)-5-(benzyloxy)pent-3-en-2-yl]-2-[(2E)-4-hydroxy-4-methylpent-2-enyl]-4-(methoxymethoxy)-3-methylphenol