(2S,4S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-5-methoxy-4-methyl-pentanoic acid methyl ester

Base Information

Chemical Name:(2S,4S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-5-methoxy-4-methyl-pentanoic acid methyl ester
CAS No.:122911-37-9
Molecular Formula:C₂₈H₄₅NO₆Si
Molecular Weight:519.754
Hs Code.:

Synonyms:(2S,4S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-5-methoxy-4-methyl-pentanoic acid methyl ester

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Chemical Property of (2S,4S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-5-methoxy-4-methyl-pentanoic acid methyl ester

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Technology Process of (2S,4S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-5-methoxy-4-methyl-pentanoic acid methyl ester

There total 1 articles about (2S,4S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-5-methoxy-4-methyl-pentanoic acid methyl ester 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: 97.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 128836-50-0
(2S,4S,5R)-5-[3-(2,5-Dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-2-hydroxy-5-methoxy-4-methyl-pentanoic acid methyl ester

: 122911-37-9
(2S,4S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-5-methoxy-4-methyl-pentanoic acid methyl ester

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1039/P19900000047

Reference yield:

: 122911-37-9
(2S,4S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-5-methoxy-4-methyl-pentanoic acid methyl ester

: 122911-38-0
(2S,4S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-5-methoxy-4-methyl-pentanal

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -82 ℃; for 1h;
DOI:10.1039/P19900000047

Reference yield:

: 122911-37-9
(2S,4S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-5-methoxy-4-methyl-pentanoic acid methyl ester

: 123083-98-7
(2E,4Z,6S,7R,8E,10S,11R,12S,14S,15R)-15-(3-Amino-2,5-dimethoxyphenyl)-7-(tert-butyldimethylsiloxy)-11,12,15-trimethoxy-2,6,8,10,14-pentamethyl-2,4,8-pentadecatrienoic acid

Guidance literature:: Multi-step reaction with 16 steps

1: DIBAL-H / toluene / 1 h / -82 °C

2: 91 percent / CrCl₂ / tetrahydrofuran / 5 h / Ambient temperature

3: 97 percent / TBAF / tetrahydrofuran / 16 h / Ambient temperature

4: 1.) (L)-(+)-DIPT, Ti(i-PrO)4, 2.) TBHP / 1.) CH₂Cl₂, 30 min, -20 deg C, 2.) CH₂Cl₂, i-Octane, -20 deg C, 23 h

5: 88 percent / NaH / tetrahydrofuran / 1.) -15 deg C, 15 min, 2.) 0 deg C, 3 h

7: 96 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) room temperature, 6 h

8: 96 percent / HF*Py-Py-THF / methanol / 6.5 h / Ambient temperature

9: 89 percent / SO₃*Py, DMSO, NEt₃ / tetrahydrofuran / 0.25 h / Ambient temperature

10: 1.) KN(SiMe₃)2 / 1.) 18-crown-6 / 1.) toluene, THF, 10 min, -80 degC, 2.) THF, 1 h, -78 deg C

11: 99 percent / DIBAL-H / toluene / 1 h / -33 °C

12: 70 percent / Hydroxylamine Hydrochloride, KOH / ethanol; H₂O / 48 h / Heating

13: 95 percent / NEt₃ / CH₂Cl₂ / 0.67 h / Ambient temperature

14: 95 percent / Pyridinium dichromate / CH₂Cl₂ / 6.5 h / Ambient temperature

15: CH₂Cl₂ / 40 h / Heating

16: LiOH / tetrahydrofuran; methanol; H₂O / 24 h / Ambient temperature

With tetrahydrofuran; pyridine; chromium dichloride; titanium(IV) isopropylate; tert.-butylhydroperoxide; potassium hydroxide; lithium hydroxide; dipyridinium dichromate; pyridine-SO₃ complex; L-(+)-diisopropyl tartrate; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; 18-crown-6 ether; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; toluene;
DOI:10.1039/P19900000047