(2S,3S,4R,8S,10R)-1,3-bis(tert-butyldimethylsilanyloxy)-10-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2,4,8-trimethylundecan-5-one

Base Information

Chemical Name:(2S,3S,4R,8S,10R)-1,3-bis(tert-butyldimethylsilanyloxy)-10-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2,4,8-trimethylundecan-5-one
CAS No.:845780-44-1
Molecular Formula:C₃₈H₇₀O₆Si₂
Molecular Weight:679.141
Hs Code.:

Synonyms:(2S,3S,4R,8S,10R)-1,3-bis(tert-butyldimethylsilanyloxy)-10-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2,4,8-trimethylundecan-5-one

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Chemical Property of (2S,3S,4R,8S,10R)-1,3-bis(tert-butyldimethylsilanyloxy)-10-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2,4,8-trimethylundecan-5-one

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Technology Process of (2S,3S,4R,8S,10R)-1,3-bis(tert-butyldimethylsilanyloxy)-10-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2,4,8-trimethylundecan-5-one

There total 12 articles about (2S,3S,4R,8S,10R)-1,3-bis(tert-butyldimethylsilanyloxy)-10-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2,4,8-trimethylundecan-5-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: 88.0%

: 845780-33-8
(2S,3S,4R,8R,10R)-1,3-bis(tert-butyldimethylsilanyloxy)-10-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2,4,8-trimethylundec-6-en-5-one

: 845780-44-1
(2S,3S,4R,8S,10R)-1,3-bis(tert-butyldimethylsilanyloxy)-10-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2,4,8-trimethylundecan-5-one

Guidance literature:: With sodium tetrahydroborate; nickel dichloride; In methanol; at 0 ℃; for 0.75h;
DOI:10.1021/ol0478279

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 845780-44-1
(2S,3S,4R,8S,10R)-1,3-bis(tert-butyldimethylsilanyloxy)-10-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2,4,8-trimethylundecan-5-one

Guidance literature:: Multi-step reaction with 3 steps

1: 818 mg / tetrahydrofuran; hexane; heptane / -78 - 20 °C

2: 83 mg / Ba(OH)2*8H₂O / tetrahydrofuran; H₂O / 6 h / 20 °C

3: 88 percent / NiCl₂*6H₂O; NaBH₄ / methanol / 0.75 h / 0 °C

With barium dihydroxide; sodium tetrahydroborate; nickel dichloride; In tetrahydrofuran; methanol; hexane; n-heptane; water; 2: Horner-Wadsworth-Emmons coupling;
DOI:10.1021/ol0478279

Reference yield:

: 444105-66-2
(3R,4S,5S)-4-[(tert-butyldimethylsilanyl)oxy]-3,5-dimethyltetrahydropyran-2-one

: 845780-44-1
(2S,3S,4R,8S,10R)-1,3-bis(tert-butyldimethylsilanyloxy)-10-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2,4,8-trimethylundecan-5-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.25 h / -78 °C

1.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

1.3: LDA / tetrahydrofuran; hexane; heptane / 0.5 h / -78 °C

2.1: 818 mg / tetrahydrofuran; hexane; heptane / -78 - 20 °C

3.1: 83 mg / Ba(OH)2*8H₂O / tetrahydrofuran; H₂O / 6 h / 20 °C

4.1: 88 percent / NiCl₂*6H₂O; NaBH₄ / methanol / 0.75 h / 0 °C

With barium dihydroxide; sodium tetrahydroborate; n-butyllithium; nickel dichloride; In tetrahydrofuran; methanol; hexane; n-heptane; water; 3.1: Horner-Wadsworth-Emmons coupling;
DOI:10.1021/ol0478279