[(1S,2S)-1-((2S,3R)-3-Benzyloxymethyl-oxiranylmethyl)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propoxy]-triisopropyl-silane

Base Information

Chemical Name:[(1S,2S)-1-((2S,3R)-3-Benzyloxymethyl-oxiranylmethyl)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propoxy]-triisopropyl-silane
CAS No.:842141-83-7
Molecular Formula:C₂₈H₄₈O₅Si
Molecular Weight:492.772
Hs Code.:

Synonyms:[(1S,2S)-1-((2S,3R)-3-Benzyloxymethyl-oxiranylmethyl)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propoxy]-triisopropyl-silane

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Chemical Property of [(1S,2S)-1-((2S,3R)-3-Benzyloxymethyl-oxiranylmethyl)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propoxy]-triisopropyl-silane

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Technology Process of [(1S,2S)-1-((2S,3R)-3-Benzyloxymethyl-oxiranylmethyl)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propoxy]-triisopropyl-silane

There total 8 articles about [(1S,2S)-1-((2S,3R)-3-Benzyloxymethyl-oxiranylmethyl)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propoxy]-triisopropyl-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: 80.0%

: 100-39-0
benzyl bromide

: 842141-85-9
{(2R,3S)-3-[(2S,3S)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-triisopropylsilanyloxy-butyl]-oxiranyl}-methanol

: 842141-83-7
[(1S,2S)-1-((2S,3R)-3-Benzyloxymethyl-oxiranylmethyl)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propoxy]-triisopropyl-silane

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride;
DOI:10.1055/s-2004-835661

Reference yield:

: 756834-72-7
(3S,4S)-3-methyl-6-<(tert-butyldimethylsilyl)oxy>-1-hexen-4-ol

: 842141-83-7
[(1S,2S)-1-((2S,3R)-3-Benzyloxymethyl-oxiranylmethyl)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propoxy]-triisopropyl-silane

Guidance literature:: Multi-step reaction with 8 steps

1: 97 percent / 2,6-lutidine / CH₂Cl₂

2: 24 percent / OsO₄; aq. NMO / tetrahydrofuran

3: 76 percent / p-TsOH; CuSO₄ / 20 °C

4: 81 percent / TPAP; NMO; molecular sieves / CH₂Cl₂

5: 91 percent / 18-crown-6; KHMDS / tetrahydrofuran / -78 °C

6: 99 percent / DIBAL-H / CH₂Cl₂ / -78 °C

7: 56 percent / D-DET; Ti(O-i-Pr)4; t-BuOOH / molecular sieves

8: 80 percent / NaH; Bu₄NI

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; osmium(VIII) oxide; N-methyl-2-indolinone; molecular sieve; tetrapropylammonium perruthennate; 18-crown-6 ether; diethyl (2S,3S)-tartrate; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; copper(II) sulfate; molecular sieve; In tetrahydrofuran; dichloromethane;
DOI:10.1055/s-2004-835661

Reference yield:

: 842141-80-4
(3S,4S)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-triisopropylsilanyloxy-pentanal

: 842141-83-7
[(1S,2S)-1-((2S,3R)-3-Benzyloxymethyl-oxiranylmethyl)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propoxy]-triisopropyl-silane

Guidance literature:: Multi-step reaction with 4 steps

1: 91 percent / 18-crown-6; KHMDS / tetrahydrofuran / -78 °C

2: 99 percent / DIBAL-H / CH₂Cl₂ / -78 °C

3: 56 percent / D-DET; Ti(O-i-Pr)4; t-BuOOH / molecular sieves

4: 80 percent / NaH; Bu₄NI

With titanium(IV) isopropylate; tert.-butylhydroperoxide; 18-crown-6 ether; diethyl (2S,3S)-tartrate; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; molecular sieve; In tetrahydrofuran; dichloromethane;
DOI:10.1055/s-2004-835661