(3E,2S,4'R,5'R)-(tert-butyldimethylsilyl) 4-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]but-3-en-2-yl ether

Base Information

Chemical Name:(3E,2S,4'R,5'R)-(tert-butyldimethylsilyl) 4-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]but-3-en-2-yl ether
CAS No.:844499-05-4
Molecular Formula:C₄₀H₄₉BO₅Si
Molecular Weight:648.723
Hs Code.:

Synonyms:(3E,2S,4'R,5'R)-(tert-butyldimethylsilyl) 4-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]but-3-en-2-yl ether

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Chemical Property of (3E,2S,4'R,5'R)-(tert-butyldimethylsilyl) 4-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]but-3-en-2-yl ether

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Technology Process of (3E,2S,4'R,5'R)-(tert-butyldimethylsilyl) 4-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]but-3-en-2-yl ether

There total 2 articles about (3E,2S,4'R,5'R)-(tert-butyldimethylsilyl) 4-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]but-3-en-2-yl ether 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:

: 130874-89-4
(2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenyl-2,3-butandiol

: 150406-34-1
(S)-3-(tert-butyldimethylsilyloxy)but-1-yne

: 844499-05-4
(3E,2S,4'R,5'R)-(tert-butyldimethylsilyl) 4-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]but-3-en-2-yl ether

Guidance literature:: (S)-3-(tert-butyldimethylsilyloxy)but-1-yne; With bis(cyclohexanyl)borane; In 1,2-dimethoxyethane; at 20 ℃; for 1h;

With trimethylamine-N-oxide; In 1,2-dimethoxyethane; for 1h;

(2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenyl-2,3-butandiol; In 1,2-dimethoxyethane; Further stages.;
DOI:10.1002/ejoc.200400572

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 844499-05-4
(3E,2S,4'R,5'R)-(tert-butyldimethylsilyl) 4-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]but-3-en-2-yl ether

Guidance literature:: Multi-step reaction with 2 steps

1.1: 85 percent / imidazole / CH₂Cl₂ / 5 h / 20 °C

2.1: Cy₂BH / 1,2-dimethoxy-ethane / 1 h / 20 °C

2.2: trimethylamine N-oxide dihydrate / 1,2-dimethoxy-ethane / 1 h

2.3: 1,2-dimethoxy-ethane

With 1H-imidazole; bis(cyclohexanyl)borane; In 1,2-dimethoxyethane; dichloromethane;
DOI:10.1002/ejoc.200400572

Reference yield: 78.0%

: 844499-05-4
(3E,2S,4'R,5'R)-(tert-butyldimethylsilyl) 4-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]but-3-en-2-yl ether

: (3E,2S,4'R,5'R)-4-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]but-3-en-2-ol

Guidance literature:: With hydrogenchloride; water; In methanol; dichloromethane; at 60 ℃; for 0.25h; Inert atmosphere; Microwave irradiation;
DOI:10.1016/j.tet.2010.04.100