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

Base Information

Chemical Name:(2S,3R,4S,5R)-4-Benzyloxy-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-vinyl-tetrahydro-furan-2,3-diol
CAS No.:291506-97-3
Molecular Formula:C₂₁H₃₄O₅Si
Molecular Weight:394.583
Hs Code.:

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

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Chemical Property of (2S,3R,4S,5R)-4-Benzyloxy-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-vinyl-tetrahydro-furan-2,3-diol

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Technology Process of (2S,3R,4S,5R)-4-Benzyloxy-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-vinyl-tetrahydro-furan-2,3-diol

There total 4 articles about (2S,3R,4S,5R)-4-Benzyloxy-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-vinyl-tetrahydro-furan-2,3-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: 81.0%

: 228122-14-3
[2-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-tert-butyl-dimethyl-silane

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

Guidance literature:: With titanium tetrachloride; In dichloromethane; at -78 - 20 ℃; for 12h;
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

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

Guidance literature:: Multi-step reaction with 4 steps

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

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

3: 96 percent / NaH; tetra-n-butylammonium iodide / dimethylformamide; tetrahydrofuran / 0 - 20 °C

4: 81 percent / TiCl₄ / CH₂Cl₂ / 12 h / -78 - 20 °C

With titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Oxidation / 2: Addition / 3: Alkylation / 4: deacetalization;
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

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

Guidance literature:: Multi-step reaction with 3 steps

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

2: 96 percent / NaH; tetra-n-butylammonium iodide / dimethylformamide; tetrahydrofuran / 0 - 20 °C

3: 81 percent / TiCl₄ / CH₂Cl₂ / 12 h / -78 - 20 °C

With titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Addition / 2: Alkylation / 3: deacetalization;
DOI:10.1002/1099-0690(200006)2000:12<2187::AID-EJOC2187<3.0.CO;2-2