(1S,2R)-2-[benzyl(mesitylenyl)sulfonylamino]-1-phenylpropyl (2S,3S,5R,6R,8S)-3-(tert-butyldimethylsilyloxy)-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonanoate

Base Information

Chemical Name:(1S,2R)-2-[benzyl(mesitylenyl)sulfonylamino]-1-phenylpropyl (2S,3S,5R,6R,8S)-3-(tert-butyldimethylsilyloxy)-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonanoate
CAS No.:944943-17-3
Molecular Formula:C₆₃H₁₀₁NO₉SSi₃
Molecular Weight:1132.82
Hs Code.:

(1S,2R)-2-[benzyl(mesitylenyl)sulfonylamino]-1-phenylpropyl (2S,3S,5R,6R,8S)-3-(tert-butyldimethylsilyloxy)-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonanoate

Synonyms:(1S,2R)-2-[benzyl(mesitylenyl)sulfonylamino]-1-phenylpropyl (2S,3S,5R,6R,8S)-3-(tert-butyldimethylsilyloxy)-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonanoate

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Chemical Property of (1S,2R)-2-[benzyl(mesitylenyl)sulfonylamino]-1-phenylpropyl (2S,3S,5R,6R,8S)-3-(tert-butyldimethylsilyloxy)-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonanoate

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Technology Process of (1S,2R)-2-[benzyl(mesitylenyl)sulfonylamino]-1-phenylpropyl (2S,3S,5R,6R,8S)-3-(tert-butyldimethylsilyloxy)-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonanoate

There total 11 articles about (1S,2R)-2-[benzyl(mesitylenyl)sulfonylamino]-1-phenylpropyl (2S,3S,5R,6R,8S)-3-(tert-butyldimethylsilyloxy)-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonanoate 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:

: 944943-15-1
(1S,2R)-2-[benzyl(mesitylenyl)sulfonylamino]-1-phenylpropyl (2S,3S,5R,6R,8S)-3-hydroxy-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonanoate

: 69739-34-0
t-butyldimethylsiyl triflate

: 944943-17-3
(1S,2R)-2-[benzyl(mesitylenyl)sulfonylamino]-1-phenylpropyl (2S,3S,5R,6R,8S)-3-(tert-butyldimethylsilyloxy)-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonanoate

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 3h;
DOI:10.1021/ol0710360

Reference yield:

: 763-32-6
2-methyl-1-buten-4-ol

: 944943-17-3
(1S,2R)-2-[benzyl(mesitylenyl)sulfonylamino]-1-phenylpropyl (2S,3S,5R,6R,8S)-3-(tert-butyldimethylsilyloxy)-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonanoate

Guidance literature:: Multi-step reaction with 11 steps

1.1: 95 percent / triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 3 h / Heating

2.1: 99 percent / AD-mix-β / H2O; 2-methyl-propan-2-ol / 4 h / 0 °C

3.1: 98 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h / 20 °C

4.1: 81 percent / ammonium cerium(IV) nitrate / H₂O; acetonitrile / 0.17 h / 0 °C

5.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

6.1: 92 percent / EtMgBr / diethyl ether / 3 h / 20 °C

7.1: 95 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

8.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

9.1: triethylamine / CH₂Cl₂; hexane / 1 h / -78 °C

9.2: CH₂Cl₂; hexane / -78 - 20 °C

9.3: methanol; hydrogen peroxide / CH₂Cl₂; hexane

10.1: 2,6-lutidine / CH₂Cl₂ / 3 h / -78 °C

With 2,6-dimethylpyridine; dmap; ammonium cerium(IV) nitrate; di-isopropyl azodicarboxylate; AD-mix-β; ethylmagnesium bromide; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol; 7.1: Dess-Martin oxidation / 9.1: Dess-Martin oxidation;
DOI:10.1021/ol0710360

Reference yield:

: 237393-21-4
(R)-2-hydroxy-4-(4-methoxyphenoxy)-2-methylbutyl 2,2,2-trimethylacetate

: 944943-17-3
(1S,2R)-2-[benzyl(mesitylenyl)sulfonylamino]-1-phenylpropyl (2S,3S,5R,6R,8S)-3-(tert-butyldimethylsilyloxy)-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonanoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 81 percent / ammonium cerium(IV) nitrate / H₂O; acetonitrile / 0.17 h / 0 °C

2.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

3.1: 92 percent / EtMgBr / diethyl ether / 3 h / 20 °C

4.1: 95 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

5.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

6.1: triethylamine / CH₂Cl₂; hexane / 1 h / -78 °C

6.2: CH₂Cl₂; hexane / -78 - 20 °C

6.3: methanol; hydrogen peroxide / CH₂Cl₂; hexane

7.1: 2,6-lutidine / CH₂Cl₂ / 3 h / -78 °C

With 2,6-dimethylpyridine; ammonium cerium(IV) nitrate; ethylmagnesium bromide; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; In diethyl ether; hexane; dichloromethane; water; acetonitrile; 4.1: Dess-Martin oxidation / 6.1: Dess-Martin oxidation;
DOI:10.1021/ol0710360