(2S,3R)-2-(benzyloxy)-5-(tert-butyldimethylsiloxy)-2-vinyl-1,3-pentanediol

Base Information

Chemical Name:(2S,3R)-2-(benzyloxy)-5-(tert-butyldimethylsiloxy)-2-vinyl-1,3-pentanediol
CAS No.:228122-15-4
Molecular Formula:C₂₀H₃₄O₄Si
Molecular Weight:366.573
Hs Code.:

Synonyms:(2S,3R)-2-(benzyloxy)-5-(tert-butyldimethylsiloxy)-2-vinyl-1,3-pentanediol

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Chemical Property of (2S,3R)-2-(benzyloxy)-5-(tert-butyldimethylsiloxy)-2-vinyl-1,3-pentanediol

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Technology Process of (2S,3R)-2-(benzyloxy)-5-(tert-butyldimethylsiloxy)-2-vinyl-1,3-pentanediol

There total 5 articles about (2S,3R)-2-(benzyloxy)-5-(tert-butyldimethylsiloxy)-2-vinyl-1,3-pentanediol 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: 76.0%

: 291506-97-3
(2S,3R,4S,5R)-4-Benzyloxy-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-vinyl-tetrahydro-furan-2,3-diol

: 228122-15-4
(2S,3R)-2-(benzyloxy)-5-(tert-butyldimethylsiloxy)-2-vinyl-1,3-pentanediol

Guidance literature:: (2S,3R,4S,5R)-4-Benzyloxy-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-vinyl-tetrahydro-furan-2,3-diol; With Dess-Martin periodane; In dichloromethane; for 0.333333h;

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h; Further stages.;
DOI:10.1002/1099-0690(200006)2000:12<2187::AID-EJOC2187<3.0.CO;2-2

Reference yield:

: 189165-94-4
(3aR,5R,6S,6aR)-5-<2-(tert-butyldimethylsiloxy)ethyl>-tetrahydro-2,2-dimethylfuro<2,3-d>-1,3-dioxol-6-ol

: 228122-15-4
(2S,3R)-2-(benzyloxy)-5-(tert-butyldimethylsiloxy)-2-vinyl-1,3-pentanediol

Guidance literature:: Multi-step reaction with 5 steps

1.1: Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

2.1: diethyl ether; tetrahydrofuran / 0.33 h / -78 °C

3.1: 96 percent / NaH; tetra-n-butylammonium iodide / dimethylformamide; tetrahydrofuran / 0 - 20 °C

4.1: 81 percent / TiCl₄ / CH₂Cl₂ / 12 h / -78 - 20 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 0.33 h

5.2: 76 percent / NaBH₄ / methanol / 0.5 h / 0 °C

With titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1.1: Oxidation / 2.1: Addition / 3.1: Alkylation / 4.1: deacetalization / 5.1: Oxidation / 5.2: Reduction;
DOI:10.1002/1099-0690(200006)2000:12<2187::AID-EJOC2187<3.0.CO;2-2

Reference yield:

: 220325-36-0
(3aR,5R,6aR)-5-<2-(tert-butyldimethylsiloxy)ethyl>dihydro-2,2-dimethylfuro<2,3-d>-1,3-dioxol-6(5H)-one

: 228122-15-4
(2S,3R)-2-(benzyloxy)-5-(tert-butyldimethylsiloxy)-2-vinyl-1,3-pentanediol

Guidance literature:: Multi-step reaction with 4 steps

1.1: diethyl ether; tetrahydrofuran / 0.33 h / -78 °C

2.1: 96 percent / NaH; tetra-n-butylammonium iodide / dimethylformamide; tetrahydrofuran / 0 - 20 °C

3.1: 81 percent / TiCl₄ / CH₂Cl₂ / 12 h / -78 - 20 °C

4.1: Dess-Martin periodinane / CH₂Cl₂ / 0.33 h

4.2: 76 percent / NaBH₄ / methanol / 0.5 h / 0 °C

With titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1.1: Addition / 2.1: Alkylation / 3.1: deacetalization / 4.1: Oxidation / 4.2: Reduction;
DOI:10.1002/1099-0690(200006)2000:12<2187::AID-EJOC2187<3.0.CO;2-2