(2R,3R,4E)-2-(benzyloxy)-2-[2-(tert-butyldimethylsiloxy)ethyl]hex-4-ene-1,3-diol

Base Information

Chemical Name:(2R,3R,4E)-2-(benzyloxy)-2-[2-(tert-butyldimethylsiloxy)ethyl]hex-4-ene-1,3-diol
CAS No.:865308-24-3
Molecular Formula:C₂₁H₃₆O₄Si
Molecular Weight:380.6
Hs Code.:

Synonyms:(2R,3R,4E)-2-(benzyloxy)-2-[2-(tert-butyldimethylsiloxy)ethyl]hex-4-ene-1,3-diol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3R,4E)-2-(benzyloxy)-2-[2-(tert-butyldimethylsiloxy)ethyl]hex-4-ene-1,3-diol

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Technology Process of (2R,3R,4E)-2-(benzyloxy)-2-[2-(tert-butyldimethylsiloxy)ethyl]hex-4-ene-1,3-diol

There total 2 articles about (2R,3R,4E)-2-(benzyloxy)-2-[2-(tert-butyldimethylsiloxy)ethyl]hex-4-ene-1,3-diol 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: 99.0%

: methyl (4E)-2-benzyloxy-2-(2-[t-butyldimethylsiloxy]ethyl)-3-hydroxyhex-4-enoate

: 865308-24-3
(2R,3R,4E)-2-(benzyloxy)-2-[2-(tert-butyldimethylsiloxy)ethyl]hex-4-ene-1,3-diol

Guidance literature:: With sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; at -45 - 0 ℃; for 1.33333h;
DOI:10.1039/b507401k

Reference yield: 99.0%

: methyl (2S,3R,4E)-2-(benzyloxy)-2-[2-(tert-butyldimethylsiloxy)ethyl]-3-hydroxyhex-4-enoate

: 865308-24-3
(2R,3R,4E)-2-(benzyloxy)-2-[2-(tert-butyldimethylsiloxy)ethyl]hex-4-ene-1,3-diol

Guidance literature:: With sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; at -45 - 0 ℃; for 1.33333h; Inert atmosphere;
DOI:10.1055/s-0029-1216922

Reference yield:

: 865308-24-3
(2R,3R,4E)-2-(benzyloxy)-2-[2-(tert-butyldimethylsiloxy)ethyl]hex-4-ene-1,3-diol

: 865308-34-5
((1S,5S,7R)-7-(cumyldimethylsiloxy)-5-methyl-4,8-dioxabicyclo[3.2.1]octyl)formaldehyde

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / lithium 4,4'-di-tert-butylbiphenylide / tetrahydrofuran / 9 h / -78 °C

2: 71 percent / Et₃N / CH₂Cl₂ / 20 h / 0 °C

3: 93 percent / pyridine / toluene / 2 h / 0 °C

4: 98 percent / aq. HCl / tetrahydrofuran / 1.5 h / 0 °C

5: 91 percent / PdCl₂ / dimethylformamide / 0 °C

6: 100 percent / K₂CO₃ / methanol / 0.5 h / 20 °C

7: 100 percent / NCS; K₂CO₃; 4 Angstroem molecular sieves / N-t-butylbenzenesulfenamide / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; hydrogenchloride; N-chloro-succinimide; 4,4'-di(tert-butyl)-[1,1-biphenyl]yllithium; 4 A molecular sieve; potassium carbonate; triethylamine; palladium dichloride; N-(phenylthio)-N-(tert-butyl)amine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1039/b507401k