[(1R,2S)-1-allyl-2-((1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-5-methyl-hex-4-enyloxy]-tert-butyl-dimethyl-silane

Base Information

Chemical Name:[(1R,2S)-1-allyl-2-((1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-5-methyl-hex-4-enyloxy]-tert-butyl-dimethyl-silane
CAS No.:558459-25-9
Molecular Formula:C₃₀H₅₀O₃Si
Molecular Weight:486.811
Hs Code.:

Synonyms:[(1R,2S)-1-allyl-2-((1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-5-methyl-hex-4-enyloxy]-tert-butyl-dimethyl-silane

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Chemical Property of [(1R,2S)-1-allyl-2-((1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-5-methyl-hex-4-enyloxy]-tert-butyl-dimethyl-silane

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Technology Process of [(1R,2S)-1-allyl-2-((1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-5-methyl-hex-4-enyloxy]-tert-butyl-dimethyl-silane

There total 11 articles about [(1R,2S)-1-allyl-2-((1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-5-methyl-hex-4-enyloxy]-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: 99.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 558459-37-3
5-[(1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy]-(4R,5S)-8-methyl-nona-1,7-dien-4-ol

: 558459-25-9
[(1R,2S)-1-allyl-2-((1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-5-methyl-hex-4-enyloxy]-tert-butyl-dimethyl-silane

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; for 1.5h;
DOI:10.1021/ja029956v

Reference yield:

: 924-41-4
1,5-hexadiene-3-ol

: 558459-25-9
[(1R,2S)-1-allyl-2-((1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-5-methyl-hex-4-enyloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 11 steps

1.1: (-)-dicyclohexyl tartrate; Ti(OiPr)4; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / -20 °C

1.2: 42 percent / t-BuOOH / CH₂Cl₂ / 19 h / -20 °C

2.1: 87 percent / Bu₄NI; NaH / tetrahydrofuran / -78 - 25 °C

3.1: 90 percent / CuI / tetrahydrofuran; diethyl ether / 1 h / -20 °C

4.1: NaH / tetrahydrofuran / 0 - 25 °C

4.2: 90 percent / tetrahydrofuran / 10 h / 25 °C

5.1: Et₃N / diethyl ether / -78 - 0 °C

6.1: n-BuLi / tetrahydrofuran; hexane

6.2: 28.6 g / tetrahydrofuran; hexane / -78 - 0 °C

7.1: NaN(SiMe₃)2 / tetrahydrofuran / 0.5 h / -78 °C

7.2: 82 percent / tetrahydrofuran / 1.5 h / -40 °C

8.1: 82 percent / NaBH₄ / tetrahydrofuran; H₂O / 14 h / 25 °C

9.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -15 °C

10.1: methoxyborane derived from 2-carene / diethyl ether / 1 h

10.2: diethyl ether / 2 h

10.3: aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 3 h / Heating

11.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h

With 2,6-dimethylpyridine; titanium(IV) isopropylate; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; oxalyl dichloride; (-)-dicyclohexyl D-tartrate; 4 A molecular sieve; methoxyborane derived from 2-carene; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; 9.1: Swern oxidation;
DOI:10.1021/ja029956v

Reference yield:

: 558459-27-1
(1R)-1-[(1S)-oxiranyl]-but-3-en-1-ol

: 558459-25-9
[(1R,2S)-1-allyl-2-((1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-5-methyl-hex-4-enyloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 10 steps

1.1: 87 percent / Bu₄NI; NaH / tetrahydrofuran / -78 - 25 °C

2.1: 90 percent / CuI / tetrahydrofuran; diethyl ether / 1 h / -20 °C

3.1: NaH / tetrahydrofuran / 0 - 25 °C

3.2: 90 percent / tetrahydrofuran / 10 h / 25 °C

4.1: Et₃N / diethyl ether / -78 - 0 °C

5.1: n-BuLi / tetrahydrofuran; hexane

5.2: 28.6 g / tetrahydrofuran; hexane / -78 - 0 °C

6.1: NaN(SiMe₃)2 / tetrahydrofuran / 0.5 h / -78 °C

6.2: 82 percent / tetrahydrofuran / 1.5 h / -40 °C

7.1: 82 percent / NaBH₄ / tetrahydrofuran; H₂O / 14 h / 25 °C

8.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -15 °C

9.1: methoxyborane derived from 2-carene / diethyl ether / 1 h

9.2: diethyl ether / 2 h

9.3: aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 3 h / Heating

10.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h

With 2,6-dimethylpyridine; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; oxalyl dichloride; methoxyborane derived from 2-carene; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; 8.1: Swern oxidation;
DOI:10.1021/ja029956v