(2R,5S,6R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-6-((3S,5S)-3,5,7-trimethyl-oct-7-en-1-ynyl)-phenyl]-5-methyl-6-((S)-3-methyl-pent-4-enyl)-[1,3]dioxan-4-one

Base Information

Chemical Name:(2R,5S,6R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-6-((3S,5S)-3,5,7-trimethyl-oct-7-en-1-ynyl)-phenyl]-5-methyl-6-((S)-3-methyl-pent-4-enyl)-[1,3]dioxan-4-one
CAS No.:887137-73-7
Molecular Formula:C₃₇H₅₈O₆Si
Molecular Weight:626.949
Hs Code.:

(2R,5S,6R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-6-((3S,5S)-3,5,7-trimethyl-oct-7-en-1-ynyl)-phenyl]-5-methyl-6-((S)-3-methyl-pent-4-enyl)-[1,3]dioxan-4-one

Synonyms:(2R,5S,6R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-6-((3S,5S)-3,5,7-trimethyl-oct-7-en-1-ynyl)-phenyl]-5-methyl-6-((S)-3-methyl-pent-4-enyl)-[1,3]dioxan-4-one

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Chemical Property of (2R,5S,6R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-6-((3S,5S)-3,5,7-trimethyl-oct-7-en-1-ynyl)-phenyl]-5-methyl-6-((S)-3-methyl-pent-4-enyl)-[1,3]dioxan-4-one

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Technology Process of (2R,5S,6R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-6-((3S,5S)-3,5,7-trimethyl-oct-7-en-1-ynyl)-phenyl]-5-methyl-6-((S)-3-methyl-pent-4-enyl)-[1,3]dioxan-4-one

There total 18 articles about (2R,5S,6R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-6-((3S,5S)-3,5,7-trimethyl-oct-7-en-1-ynyl)-phenyl]-5-methyl-6-((S)-3-methyl-pent-4-enyl)-[1,3]dioxan-4-one 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: 26.0%

: 853995-88-7
(2S,3R,6S)-3-Hydroxy-2,6-dimethyl-oct-7-enoic acid

: 887137-72-6
2-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-6-((3S,5S)-3,5,7-trimethyl-oct-7-en-1-ynyl)-benzaldehyde

: 887137-73-7
(2R,5S,6R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-6-((3S,5S)-3,5,7-trimethyl-oct-7-en-1-ynyl)-phenyl]-5-methyl-6-((S)-3-methyl-pent-4-enyl)-[1,3]dioxan-4-one

Guidance literature:: With isopropoxytrimethylsilane; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 12h;
DOI:10.1021/ja060369+

Reference yield:

: 853996-02-8
(R)-5-Iodo-2,4-dimethyl-pent-1-ene

: 887137-73-7
(2R,5S,6R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-6-((3S,5S)-3,5,7-trimethyl-oct-7-en-1-ynyl)-phenyl]-5-methyl-6-((S)-3-methyl-pent-4-enyl)-[1,3]dioxan-4-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: LDA; LiCl / tetrahydrofuran; hexane / 1.33 h / -78 - 20 °C

1.2: 98 percent / tetrahydrofuran; hexane / 14 h / 20 °C

2.1: 97 percent / LDA; BH₃*NH₃ / tetrahydrofuran; hexane / 3 h / 20 °C

3.1: 89 percent / Et₃N; SO₃*Py; DMSO / CH₂Cl₂ / 1 h / 0 °C

4.1: t-BuOK / tetrahydrofuran / 0.25 h / -78 °C

4.2: 77 percent / tetrahydrofuran / 1 h / -78 °C

5.1: 85 percent / PdCl₂(PPh₃)2; CuI; diisopropylamine / 6.5 h / 60 °C

6.1: 26 percent / isopropyloxytrimethylsilane; TMSOTf / CH₂Cl₂ / 12 h / -20 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; borane-ammonia complex; pyridine-SO₃ complex; isopropoxytrimethylsilane; trimethylsilyl trifluoromethanesulfonate; potassium tert-butylate; dimethyl sulfoxide; triethylamine; diisopropylamine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; 1.2: Myers alkylation / 3.1: Parikh-Doering oxidation / 5.1: Sonogashira reaction / 6.1: Kurihara condensation;
DOI:10.1021/ja060369+

Reference yield:

: 853995-87-6
2-bromo-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-benzaldehyde

: 887137-73-7
(2R,5S,6R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-6-((3S,5S)-3,5,7-trimethyl-oct-7-en-1-ynyl)-phenyl]-5-methyl-6-((S)-3-methyl-pent-4-enyl)-[1,3]dioxan-4-one

Guidance literature:: Multi-step reaction with 2 steps

1: 85 percent / PdCl₂(PPh₃)2; CuI; diisopropylamine / 6.5 h / 60 °C

2: 26 percent / isopropyloxytrimethylsilane; TMSOTf / CH₂Cl₂ / 12 h / -20 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; isopropoxytrimethylsilane; trimethylsilyl trifluoromethanesulfonate; diisopropylamine; In dichloromethane; 1: Sonogashira reaction / 2: Kurihara condensation;
DOI:10.1021/ja060369+