methyl (2E,4S,5S)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-2-methyl-5-(pent-3-yloxy)hex-2-enoate

Base Information

• Chemical Name: methyl (2E,4S,5S)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-2-methyl-5-(pent-3-yloxy)hex-2-enoate
• CAS No.: 1568987-01-8
• Molecular Formula: C₂₉H₄₂O₅Si
• Molecular Weight: 498.735
• Mol file: 1568987-01-8.mol

Synonyms:methyl (2E,4S,5S)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-2-methyl-5-(pent-3-yloxy)hex-2-enoate

Chemical Property of methyl (2E,4S,5S)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-2-methyl-5-(pent-3-yloxy)hex-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2E,4S,5S)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-2-methyl-5-(pent-3-yloxy)hex-2-enoate

There total 5 articles about methyl (2E,4S,5S)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-2-methyl-5-(pent-3-yloxy)hex-2-enoate 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:

methyl (E)-3-[(4S,5S)-2,2-diethyl-5-(tert-butyldiphenylsilyl-oxymethyl)-1,3-dioxolan-4-yl]-2-methylacrylate (1568986-96-8) → methyl (2E,4S,5S)-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-2-methyl-4-(pent-3-yloxy)hex-2-enoate (1568986-99-1) + methyl (2E,4S,5S)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-2-methyl-5-(pent-3-yloxy)hex-2-enoate (1568987-01-8)

Guidance literature:

With triethylsilane; titanium tetrachloride; In dichloromethane; at -40 - -5 ℃; Overall yield = 60 %;

DOI:10.1007/s11172-013-0168-0

Reference yield:

(4S,5S)-2,2-diethyl-4,5-bis(hydroxymethyl)-1,3-dioxolane (198691-39-3) → methyl (2E,4S,5S)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-2-methyl-5-(pent-3-yloxy)hex-2-enoate (1568987-01-8)

Guidance literature:

Multi-step reaction with 4 steps

1: dipyridinium dichromate / dichloromethane / 3 h / 20 °C

2: dichloromethane / 5 h / 20 °C

3: 1H-imidazole / dichloromethane

4: triethylsilane; titanium tetrachloride / dichloromethane / -40 - -5 °C

With 1H-imidazole; triethylsilane; dipyridinium dichromate; titanium tetrachloride; In dichloromethane;

DOI:10.1007/s11172-013-0168-0

Reference yield:

(4R,5R)-dimethyl 2,2-diethyl-1,3-dioxolane-4,5-dicarboxylate (112193-28-9) → methyl (2E,4S,5S)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-2-methyl-5-(pent-3-yloxy)hex-2-enoate (1568987-01-8)

Guidance literature:

Multi-step reaction with 5 steps

1: lithium aluminium tetrahydride / diethyl ether / 4 h / 20 °C / Inert atmosphere

2: dipyridinium dichromate / dichloromethane / 3 h / 20 °C

3: dichloromethane / 5 h / 20 °C

4: 1H-imidazole / dichloromethane

5: triethylsilane; titanium tetrachloride / dichloromethane / -40 - -5 °C

With 1H-imidazole; triethylsilane; lithium aluminium tetrahydride; dipyridinium dichromate; titanium tetrachloride; In diethyl ether; dichloromethane;

DOI:10.1007/s11172-013-0168-0

upstream raw materials:

methyl (E)-3-[(4S,5S)-2,2-diethyl-5-(tert-butyldiphenylsilyl-oxymethyl)-1,3-dioxolan-4-yl]-2-methylacrylate

(4S,5S)-2,2-diethyl-4,5-bis(hydroxymethyl)-1,3-dioxolane

(4R,5R)-dimethyl 2,2-diethyl-1,3-dioxolane-4,5-dicarboxylate

C₉H₁₆O₄

Downstream raw materials:

methyl (2E,5S)-6-(tert-butyldiphenylsilyloxy)-2-methyl-4-oxo-5-(pent-3-yloxy)hex-2-enoate