(2S,4S,5R)-4-[(R,E)-1-[(tert-butyldimethylsilyl)oxy]pentadec-2-en-1-yl]-2-phenyl-1,3-dioxan-5-ol

Base Information

Chemical Name:(2S,4S,5R)-4-[(R,E)-1-[(tert-butyldimethylsilyl)oxy]pentadec-2-en-1-yl]-2-phenyl-1,3-dioxan-5-ol
CAS No.:1374871-09-6
Molecular Formula:C₃₁H₅₄O₄Si
Molecular Weight:518.853
Hs Code.:

Synonyms:(2S,4S,5R)-4-[(R,E)-1-[(tert-butyldimethylsilyl)oxy]pentadec-2-en-1-yl]-2-phenyl-1,3-dioxan-5-ol

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Chemical Property of (2S,4S,5R)-4-[(R,E)-1-[(tert-butyldimethylsilyl)oxy]pentadec-2-en-1-yl]-2-phenyl-1,3-dioxan-5-ol

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Technology Process of (2S,4S,5R)-4-[(R,E)-1-[(tert-butyldimethylsilyl)oxy]pentadec-2-en-1-yl]-2-phenyl-1,3-dioxan-5-ol

There total 5 articles about (2S,4S,5R)-4-[(R,E)-1-[(tert-butyldimethylsilyl)oxy]pentadec-2-en-1-yl]-2-phenyl-1,3-dioxan-5-ol 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: 86.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 117168-66-8,117168-56-6
(2S,4R,5R)-4-[(R)-1-hydroxypentadecyl]-2-phenyl-1,3-dioxan-5-yl methanesulfonate

: 1374871-09-6
(2S,4S,5R)-4-[(R,E)-1-[(tert-butyldimethylsilyl)oxy]pentadec-2-en-1-yl]-2-phenyl-1,3-dioxan-5-ol

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 ℃; for 3h; Inert atmosphere;
DOI:10.1055/s-0031-1289721

Reference yield:

: 1374871-07-4
C₂₅H₄₀O₄Sn

: 1374871-09-6
(2S,4S,5R)-4-[(R,E)-1-[(tert-butyldimethylsilyl)oxy]pentadec-2-en-1-yl]-2-phenyl-1,3-dioxan-5-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: tert.-butyl lithium / diethyl ether; pentane / 1.5 h / -78 - 20 °C

1.2: 0.17 h / -78 - 0 °C

1.3: 3 h / -35 - 10 °C / Inert atmosphere

2.1: pyridine / dichloromethane / 5 h / -15 °C / Inert atmosphere

3.1: palladium 10% on activated carbon; hydrogen / methanol; dichloromethane / 16 h / 20 °C / 750.08 Torr / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

With pyridine; palladium 10% on activated carbon; hydrogen; tert.-butyl lithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; pentane;
DOI:10.1055/s-0031-1289721

Reference yield:

: 1374871-06-3
(2S,4R,5R)-4-[(R,E)-1-hydroxypentadec-2-enyl]-2-phenyl-1,3-dioxan-5-ol

: 1374871-09-6
(2S,4S,5R)-4-[(R,E)-1-[(tert-butyldimethylsilyl)oxy]pentadec-2-en-1-yl]-2-phenyl-1,3-dioxan-5-ol

Guidance literature:: Multi-step reaction with 3 steps

1: pyridine / dichloromethane / 5 h / -15 °C / Inert atmosphere

2: palladium 10% on activated carbon; hydrogen / methanol; dichloromethane / 16 h / 20 °C / 750.08 Torr / Inert atmosphere

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

With pyridine; palladium 10% on activated carbon; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1055/s-0031-1289721