(R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-6-(4-methoxy-benzyloxy)-hex-2-enal

Base Information

• Chemical Name: (R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-6-(4-methoxy-benzyloxy)-hex-2-enal
• CAS No.: 290815-58-6
• Molecular Formula: C₃₇H₆₀O₇Si₂
• Molecular Weight: 673.05

Synonyms:(R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-6-(4-methoxy-benzyloxy)-hex-2-enal

Chemical Property of (R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-6-(4-methoxy-benzyloxy)-hex-2-enal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-6-(4-methoxy-benzyloxy)-hex-2-enal

There total 7 articles about (R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-6-(4-methoxy-benzyloxy)-hex-2-enal 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: 80.0%

5-(tert-butyl-dimethyl-silanyloxy)-3-[2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-3-hydroxy-6-(4-methoxy-benzyloxy)-hexanal (290815-57-5) → (R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-6-(4-methoxy-benzyloxy)-hex-2-enal (290815-58-6)

Guidance literature:

With dmap; triethylamine; trifluoroacetic anhydride; In dichloromethane; at 45 ℃; for 16h;

DOI:10.1021/ol005850y

Reference yield:

tert-butyl(1,3-dithian-2-yl)dimethylsilane (95452-06-5) → (R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-6-(4-methoxy-benzyloxy)-hex-2-enal (290815-58-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-BuLi; HMPA / tetrahydrofuran / 0.5 h / -78 °C

1.2: tetrahydrofuran / 1.5 h / -78 - 0 °C

1.3: 87 percent / tetrahydrofuran / -78 - 20 °C

2.1: 86 percent / Hg(ClO₄)*xH₂O; CaCO₃; H₂O / tetrahydrofuran / 0.3 h / 0 °C

3.1: 80 percent / tetrahydrofuran / 0.3 h / 0 °C

4.1: 76 percent / OsO₄; NaIO₄ / tetrahydrofuran; H₂O

5.1: 80 percent / TFAA; DMAP; Et₃N / CH₂Cl₂ / 16 h / 45 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium periodate; osmium(VIII) oxide; n-butyllithium; mercury(I) perchlorate; water; triethylamine; trifluoroacetic anhydride; calcium carbonate; In tetrahydrofuran; dichloromethane; water; 1.1: Metallation / 1.2: Addition / 1.3: Condensation / 2.1: Hydrolysis / 3.1: Addition / 4.1: Oxidation / 5.1: Dehydration;

DOI:10.1021/ol005850y

Reference yield:

(R)-2-(((4-methoxybenzyl)oxy)methyl)oxirane (80910-01-6,108836-41-5,144069-33-0,134733-19-0) → (R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-6-(4-methoxy-benzyloxy)-hex-2-enal (290815-58-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-BuLi; HMPA / tetrahydrofuran / 0.5 h / -78 °C

1.2: tetrahydrofuran / 1.5 h / -78 - 0 °C

1.3: 87 percent / tetrahydrofuran / -78 - 20 °C

2.1: 86 percent / Hg(ClO₄)*xH₂O; CaCO₃; H₂O / tetrahydrofuran / 0.3 h / 0 °C

3.1: 80 percent / tetrahydrofuran / 0.3 h / 0 °C

4.1: 76 percent / OsO₄; NaIO₄ / tetrahydrofuran; H₂O

5.1: 80 percent / TFAA; DMAP; Et₃N / CH₂Cl₂ / 16 h / 45 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium periodate; osmium(VIII) oxide; n-butyllithium; mercury(I) perchlorate; water; triethylamine; trifluoroacetic anhydride; calcium carbonate; In tetrahydrofuran; dichloromethane; water; 1.1: Metallation / 1.2: Addition / 1.3: Condensation / 2.1: Hydrolysis / 3.1: Addition / 4.1: Oxidation / 5.1: Dehydration;

DOI:10.1021/ol005850y

upstream raw materials:

5-(tert-butyl-dimethyl-silanyloxy)-3-[2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-3-hydroxy-6-(4-methoxy-benzyloxy)-hexanal

tert-butyl(1,3-dithian-2-yl)dimethylsilane

(R)-2-(((4-methoxybenzyl)oxy)methyl)oxirane

tert-butyldimethylsilyl chloride

Downstream raw materials:

(E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-4-[(R)-1-(1,4-dioxa-spiro[4.5]dec-2-yl)methyl]-1-(4-methoxy-benzyloxy)-hex-4-en-2-ol

Methanesulfonic acid (2R,6R)-4-[2-(tert-butyl-diphenyl-silanyloxy)-eth-(E)-ylidene]-2,6-dihydroxy-7-(4-methoxy-benzyloxy)-heptyl ester

(2R,6R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-7-(4-methoxy-benzyloxy)-heptane-1,2,6-triol

[(2S,6R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-methanol

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