[(S)-1-((2S,5R,2'S,5'R)-5'-Benzyloxymethyl-octahydro-[2,2']bifuranyl-5-yl)-undecyloxy]-tert-butyl-dimethyl-silane

Base Information

Chemical Name:[(S)-1-((2S,5R,2'S,5'R)-5'-Benzyloxymethyl-octahydro-[2,2']bifuranyl-5-yl)-undecyloxy]-tert-butyl-dimethyl-silane
CAS No.:862603-81-4
Molecular Formula:C₃₃H₅₈O₄Si
Molecular Weight:546.907
Hs Code.:

Synonyms:[(S)-1-((2S,5R,2'S,5'R)-5'-Benzyloxymethyl-octahydro-[2,2']bifuranyl-5-yl)-undecyloxy]-tert-butyl-dimethyl-silane

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Chemical Property of [(S)-1-((2S,5R,2'S,5'R)-5'-Benzyloxymethyl-octahydro-[2,2']bifuranyl-5-yl)-undecyloxy]-tert-butyl-dimethyl-silane

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Technology Process of [(S)-1-((2S,5R,2'S,5'R)-5'-Benzyloxymethyl-octahydro-[2,2']bifuranyl-5-yl)-undecyloxy]-tert-butyl-dimethyl-silane

There total 20 articles about [(S)-1-((2S,5R,2'S,5'R)-5'-Benzyloxymethyl-octahydro-[2,2']bifuranyl-5-yl)-undecyloxy]-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:

: (R)-4-Benzyloxymethyl-2-phenyl-[1,3]dioxane

: 862603-81-4
[(S)-1-((2S,5R,2'S,5'R)-5'-Benzyloxymethyl-octahydro-[2,2']bifuranyl-5-yl)-undecyloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 17 steps

1.1: aq. AcOH

1.2: NaIO₄

2.1: Et₃N

3.1: N-methylmorpholine

4.1: NaI

5.1: 95 percent / N-Bu₃SnH; Et₃B

6.1: trifluoroacetic anhydride; pyridine

6.2: 84 percent / KOAc

7.1: 96 percent / MgBr₂*Et₂O

8.1: aq. OsO₄; 4-methylmorpholine N-oxide / acetone / 1.5 h / 20 °C

9.1: aq. NaIO₄ / ethanol / 1 h / 20 °C

10.1: 1.467 g / NaBH₄ / H₂O; ethanol / 0.5 h

11.1: 90 percent / Et₃N / CH₂Cl₂ / 12 h / 0 °C

12.1: 80 percent / N-methylmorpholine / CH₂Cl₂ / 12 h / 20 °C

13.1: 93 percent / NaI / acetone / 9 h / Heating

14.1: 95 percent / N-Bu₃SnH; Et₃B / toluene; hexane / 0.5 h / -20 °C

15.1: pyridine; trifluoroacetic anhydride / acetonitrile / 0.33 h / 0 °C

15.2: 78 percent / aq. KOAc / acetonitrile / 1.33 h / 0 °C

16.1: Mg / diethyl ether / -78 °C

16.2: diethyl ether / 2 h / -78 °C

17.1: 99 percent / imidazole / CH₂Cl₂; dimethylformamide / 8 h / 20 °C

With 4-methyl-morpholine; pyridine; 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; triethyl borane; tri-n-butyl-tin hydride; magnesium; acetic acid; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic anhydride; sodium iodide; magnesium bromide; In diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 6.1: Pummerer rearrangement / 15.1: Pummerer rearrangement;
DOI:10.1021/ja0526867

Reference yield:

: (S)-3-((2S,5R)-5-Benzyloxymethyl-tetrahydro-furan-2-yl)-3-hydroxy-propionaldehyde

: 862603-81-4
[(S)-1-((2S,5R,2'S,5'R)-5'-Benzyloxymethyl-octahydro-[2,2']bifuranyl-5-yl)-undecyloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 8 steps

1.1: 1.467 g / NaBH₄ / H₂O; ethanol / 0.5 h

2.1: 90 percent / Et₃N / CH₂Cl₂ / 12 h / 0 °C

3.1: 80 percent / N-methylmorpholine / CH₂Cl₂ / 12 h / 20 °C

4.1: 93 percent / NaI / acetone / 9 h / Heating

5.1: 95 percent / N-Bu₃SnH; Et₃B / toluene; hexane / 0.5 h / -20 °C

6.1: pyridine; trifluoroacetic anhydride / acetonitrile / 0.33 h / 0 °C

6.2: 78 percent / aq. KOAc / acetonitrile / 1.33 h / 0 °C

7.1: Mg / diethyl ether / -78 °C

7.2: diethyl ether / 2 h / -78 °C

8.1: 99 percent / imidazole / CH₂Cl₂; dimethylformamide / 8 h / 20 °C

With 4-methyl-morpholine; pyridine; 1H-imidazole; sodium tetrahydroborate; triethyl borane; tri-n-butyl-tin hydride; magnesium; triethylamine; trifluoroacetic anhydride; sodium iodide; In diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 6.1: Pummerer rearrangement;
DOI:10.1021/ja0526867

Reference yield:

: 862603-72-3
(S)-1-((2S,5R)-5-Benzyloxymethyl-tetrahydro-furan-2-yl)-propane-1,3-diol

: 862603-81-4
[(S)-1-((2S,5R,2'S,5'R)-5'-Benzyloxymethyl-octahydro-[2,2']bifuranyl-5-yl)-undecyloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 7 steps

1.1: 90 percent / Et₃N / CH₂Cl₂ / 12 h / 0 °C

2.1: 80 percent / N-methylmorpholine / CH₂Cl₂ / 12 h / 20 °C

3.1: 93 percent / NaI / acetone / 9 h / Heating

4.1: 95 percent / N-Bu₃SnH; Et₃B / toluene; hexane / 0.5 h / -20 °C

5.1: pyridine; trifluoroacetic anhydride / acetonitrile / 0.33 h / 0 °C

5.2: 78 percent / aq. KOAc / acetonitrile / 1.33 h / 0 °C

6.1: Mg / diethyl ether / -78 °C

6.2: diethyl ether / 2 h / -78 °C

7.1: 99 percent / imidazole / CH₂Cl₂; dimethylformamide / 8 h / 20 °C

With 4-methyl-morpholine; pyridine; 1H-imidazole; triethyl borane; tri-n-butyl-tin hydride; magnesium; triethylamine; trifluoroacetic anhydride; sodium iodide; In diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 5.1: Pummerer rearrangement;
DOI:10.1021/ja0526867