(E)-(4S, 5S)-methyl-4-azido-6-(tert-butyldiphenylsiloxy)-5-methyl-hex-2-enoate

Base Information

Chemical Name:(E)-(4S, 5S)-methyl-4-azido-6-(tert-butyldiphenylsiloxy)-5-methyl-hex-2-enoate
CAS No.:226067-14-7
Molecular Formula:C₂₄H₃₁N₃O₃Si
Molecular Weight:437.614
Hs Code.:

Synonyms:(E)-(4S, 5S)-methyl-4-azido-6-(tert-butyldiphenylsiloxy)-5-methyl-hex-2-enoate

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Chemical Property of (E)-(4S, 5S)-methyl-4-azido-6-(tert-butyldiphenylsiloxy)-5-methyl-hex-2-enoate

Chemical Property:

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Technology Process of (E)-(4S, 5S)-methyl-4-azido-6-(tert-butyldiphenylsiloxy)-5-methyl-hex-2-enoate

There total 2 articles about (E)-(4S, 5S)-methyl-4-azido-6-(tert-butyldiphenylsiloxy)-5-methyl-hex-2-enoate 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:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 194149-69-4
(E)-(4S, 5S)-methyl-4-azido-6-hydroxy-5-methyl-hex-2-enoate

: 226067-14-7
(E)-(4S, 5S)-methyl-4-azido-6-(tert-butyldiphenylsiloxy)-5-methyl-hex-2-enoate

Guidance literature:: With 1H-imidazole;
DOI:10.1021/jo9904617

Reference yield:

: 194149-68-3
(R)-Azido-[(2R,3S,4R)-3-(dimethyl-phenyl-silanyl)-4-methyl-tetrahydro-furan-2-yl]-acetic acid methyl ester

: 226067-14-7
(E)-(4S, 5S)-methyl-4-azido-6-(tert-butyldiphenylsiloxy)-5-methyl-hex-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

1: 96 percent / SbCl₅ / CH₂Cl₂ / 15 h / -50 °C

2: imidazole / dimethylformamide / 6 h / 0 - 20 °C

With 1H-imidazole; antimonypentachloride; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja0206700

Reference yield:

: 226067-14-7
(E)-(4S, 5S)-methyl-4-azido-6-(tert-butyldiphenylsiloxy)-5-methyl-hex-2-enoate

: 141672-08-4
(-)-motuporin

Guidance literature:: Multi-step reaction with 12 steps

1.1: SnCl₂; MeOH / 6 h / 0 - 20 °C

2.1: aq. NaHCO₃ / dioxane / 24 h / 20 °C

3.1: O₃; pyridine / methanol / -78 °C

3.2: Me₂S / methanol / 7 h / -78 - 20 °C

4.1: 973 mg / CrCl₂ / tetrahydrofuran / 5 h / 20 °C

5.1: Cp₂Zr(H)Cl / tetrahydrofuran / 1 h / 50 °C

5.2: ZnCl₂ / tetrahydrofuran / 0.03 h / 20 °C

5.3: 81 percent / Pd(PPh₃)4 / tetrahydrofuran / 0.33 h / 20 °C

6.1: 95 percent / TBAF*SiO₂ / tetrahydrofuran / 4 h / 20 °C

7.1: 87 percent / TPAP; NMO; H₂O / acetonitrile / 18 h / 20 °C

8.1: 153 mg / HATU; collidine / dimethylformamide; CH₂Cl₂; toluene / 16 h / 0 - 20 °C

9.1: 95 percent / Zn; AcOH / 4 h / 20 °C

10.1: CH₂Cl₂ / 0.75 h / 20 °C

11.1: N-ethylmorpholine / CH₂Cl₂ / 0.08 h / 20 °C

11.2: 5.4 mg / HATU / CH₂Cl₂ / 24 h / 0 - 20 °C

12.1: 52 percent / Ba(OH)2 / methanol; H₂O / 24 h / 20 °C

With N-ethylmorpholine;; pyridine; chromium dichloride; 2,3,5-trimethyl-pyridine; methanol; barium dihydroxide; Schwartz's reagent; N-methyl-2-indolinone; tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; water; silica gel; sodium hydrogencarbonate; ozone; acetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; tin(ll) chloride; zinc; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 4.1: Takai homologation;
DOI:10.1021/ja0206700