[(R)-1-((4S,5R)-5-Benzyloxy-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-allyloxy]-tert-butyl-dimethyl-silane

Base Information

Chemical Name:[(R)-1-((4S,5R)-5-Benzyloxy-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-allyloxy]-tert-butyl-dimethyl-silane
CAS No.:341990-33-8
Molecular Formula:C₂₃H₃₈O₄Si
Molecular Weight:406.638
Hs Code.:

Synonyms:[(R)-1-((4S,5R)-5-Benzyloxy-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-allyloxy]-tert-butyl-dimethyl-silane

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Chemical Property of [(R)-1-((4S,5R)-5-Benzyloxy-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-allyloxy]-tert-butyl-dimethyl-silane

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Technology Process of [(R)-1-((4S,5R)-5-Benzyloxy-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-allyloxy]-tert-butyl-dimethyl-silane

There total 6 articles about [(R)-1-((4S,5R)-5-Benzyloxy-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-allyloxy]-tert-butyl-dimethyl-silane 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: 93.0%

: 100-39-0
benzyl bromide

: 341990-32-7
(4S,5R)-4-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-but-3-enyl]-2,2-dimethyl-[1,3]dioxan-5-ol

: 341990-33-8
[(R)-1-((4S,5R)-5-Benzyloxy-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-allyloxy]-tert-butyl-dimethyl-silane

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 0 - 25 ℃; for 12h;
DOI:10.1055/s-2001-11398

Reference yield:

: 176915-71-2
(E)-4-[(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-[1,3]dioxan-4-yl]-but-2-en-1-ol

: 341990-33-8
[(R)-1-((4S,5R)-5-Benzyloxy-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-allyloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / Ti(OiPr)4; tBuOOH; (-)-diethyl tartrate / molecular sieves 4 Angstroem / CH₂Cl₂; decane / 24 h / -20 °C

2: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 0 - 25 °C

3: 97 percent / NaI; NaHCO₃ / butan-2-one / 2 h / 60 °C

4: 94 percent / tBuLi / diethyl ether / 0.5 h / -78 °C

5: 93 percent / NaH; nBu₄NI / tetrahydrofuran / 12 h / 0 - 25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; (-)-diethyl tartrate; triethylamine; sodium iodide; 4 A molecular sieve; In tetrahydrofuran; diethyl ether; decane; dichloromethane; butanone; 1: Sharpless asymmetric epoxidation;
DOI:10.1055/s-2001-11398

Reference yield:

: 176915-70-1
(E)-4-[(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-[1,3]dioxan-4-yl]-but-2-enoic acid methyl ester

: 341990-33-8
[(R)-1-((4S,5R)-5-Benzyloxy-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-allyloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 6 steps

1: 81 percent / DIBAL-H / diethyl ether / 5 h / 0 - 25 °C

2: 90 percent / Ti(OiPr)4; tBuOOH; (-)-diethyl tartrate / molecular sieves 4 Angstroem / CH₂Cl₂; decane / 24 h / -20 °C

3: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 0 - 25 °C

4: 97 percent / NaI; NaHCO₃ / butan-2-one / 2 h / 60 °C

5: 94 percent / tBuLi / diethyl ether / 0.5 h / -78 °C

6: 93 percent / NaH; nBu₄NI / tetrahydrofuran / 12 h / 0 - 25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; (-)-diethyl tartrate; triethylamine; sodium iodide; 4 A molecular sieve; In tetrahydrofuran; diethyl ether; decane; dichloromethane; butanone; 2: Sharpless asymmetric epoxidation;
DOI:10.1055/s-2001-11398