(2S,4S,5S,6R,7R,8S)-8-[(4S,6S)-2,2-Dimethyl-6-((S)-1-methyl-pent-4-ynyl)-[1,3]dioxan-4-yl]-2-ethyl-5-hydroxy-7-(4-methoxy-benzyloxy)-4,6-dimethyl-nonanoic acid amide

Base Information

• Chemical Name: (2S,4S,5S,6R,7R,8S)-8-[(4S,6S)-2,2-Dimethyl-6-((S)-1-methyl-pent-4-ynyl)-[1,3]dioxan-4-yl]-2-ethyl-5-hydroxy-7-(4-methoxy-benzyloxy)-4,6-dimethyl-nonanoic acid amide
• CAS No.: 382138-98-9
• Molecular Formula: C₃₃H₅₃NO₆
• Molecular Weight: 559.787
• Mol file: 382138-98-9.mol

Synonyms:(2S,4S,5S,6R,7R,8S)-8-[(4S,6S)-2,2-Dimethyl-6-((S)-1-methyl-pent-4-ynyl)-[1,3]dioxan-4-yl]-2-ethyl-5-hydroxy-7-(4-methoxy-benzyloxy)-4,6-dimethyl-nonanoic acid amide

Chemical Property of (2S,4S,5S,6R,7R,8S)-8-[(4S,6S)-2,2-Dimethyl-6-((S)-1-methyl-pent-4-ynyl)-[1,3]dioxan-4-yl]-2-ethyl-5-hydroxy-7-(4-methoxy-benzyloxy)-4,6-dimethyl-nonanoic acid amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S,5S,6R,7R,8S)-8-[(4S,6S)-2,2-Dimethyl-6-((S)-1-methyl-pent-4-ynyl)-[1,3]dioxan-4-yl]-2-ethyl-5-hydroxy-7-(4-methoxy-benzyloxy)-4,6-dimethyl-nonanoic acid amide

There total 40 articles about (2S,4S,5S,6R,7R,8S)-8-[(4S,6S)-2,2-Dimethyl-6-((S)-1-methyl-pent-4-ynyl)-[1,3]dioxan-4-yl]-2-ethyl-5-hydroxy-7-(4-methoxy-benzyloxy)-4,6-dimethyl-nonanoic acid amide 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%

(2S,4S,5S,6S,7S,8S)-8-[(4S,6S)-2,2-Dimethyl-6-((S)-1-methyl-pent-4-ynyl)-[1,3]dioxan-4-yl]-2-ethyl-7-(4-methoxy-benzyloxy)-4,6-dimethyl-5-triethylsilanyloxy-nonanoic acid amide (382139-18-6) → (2S,4S,5S,6R,7R,8S)-8-[(4S,6S)-2,2-Dimethyl-6-((S)-1-methyl-pent-4-ynyl)-[1,3]dioxan-4-yl]-2-ethyl-5-hydroxy-7-(4-methoxy-benzyloxy)-4,6-dimethyl-nonanoic acid amide (382138-98-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1002/1521-3773(20011001)40:19<3632::AID-ANIE3632>3.0.CO;2-5

Reference yield:

6-trimethylsilanyl-hex-5-yn-1-ol (103437-52-1) → (2S,4S,5S,6R,7R,8S)-8-[(4S,6S)-2,2-Dimethyl-6-((S)-1-methyl-pent-4-ynyl)-[1,3]dioxan-4-yl]-2-ethyl-5-hydroxy-7-(4-methoxy-benzyloxy)-4,6-dimethyl-nonanoic acid amide (382138-98-9)

Guidance literature:

Multi-step reaction with 20 steps

1.1: 72 percent / pyridinium chlorochromate / dimethylformamide / 24 h

2.1: triethylamine / tetrahydrofuran / -40 - 0 °C

3.1: 6.15 g / lithium chloride / tetrahydrofuran / 20 °C

4.1: sodium hexamethyldisilazide / tetrahydrofuran / 1.33 h / -78 °C

4.2: 69 percent / tetrahydrofuran / -78 - -40 °C

5.1: 74 percent / lithium borohydride / diethyl ether; H₂O / 1 h / 0 °C

6.1: 100 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 0 °C

7.1: 2.43 g / diethyl ether / -78 - 20 °C

8.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 0 °C

9.1: (+)-B-chlorodiisopinocampheylborane; triethylamine / diethyl ether / 1 h / 0 °C

9.2: diethyl ether / 37 h / -78 - -25 °C

9.3: 48 percent / aq. hydrogen peroxide / methanol; various solvent(s) / 1 h / 0 °C / pH 7.0

10.1: 91 percent / tetramethylammonium triacetoxyborohydride; acetic acid / acetonitrile / -25 - 0 °C

11.1: 97 percent / pyridium p-toluenesulfonate / acetone

12.1: 99 percent / TBAF / tetrahydrofuran / 20 °C

13.1: 81 percent / pyridine; DMAP / CH₂Cl₂ / 1 h / 20 °C

14.1: 97 percent / imidazole / dimethylformamide / 3 h / 50 °C

15.1: 90 percent / Dibal-H / CH₂Cl₂; toluene / 2 h / -78 °C

16.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 0 °C

17.1: 2-methyl-2-butene; sodium dihydrogen phosphate monohydrate; sodium chlorite / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 0.67 h / 20 °C

18.1: 60.4 mg / ethyl acetate; diethyl ether / 1 h / 20 °C

19.1: 71 percent / dimethylaluminium amide / CH₂Cl₂ / 39 h / Heating

20.1: 97 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

With pyridine; 1H-imidazole; dmap; sodium chlorite; sodium dihydrogenphosphate; lithium borohydride; pyridium para-toluenesulfonate; (+)-β-chlorodiisopinocampheylborane; 2-methyl-but-2-ene; oxalyl dichloride; dimethylaluminium amide; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; lithium chloride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol; 6.1: Swern oxiadtion / 8.1: Swern oxiadtion;

DOI:10.1021/ja020091v

Reference yield:

6-(trimethylsilyl)hex-5-ynoic acid: (101224-43-5) → (2S,4S,5S,6R,7R,8S)-8-[(4S,6S)-2,2-Dimethyl-6-((S)-1-methyl-pent-4-ynyl)-[1,3]dioxan-4-yl]-2-ethyl-5-hydroxy-7-(4-methoxy-benzyloxy)-4,6-dimethyl-nonanoic acid amide (382138-98-9)

Guidance literature:

Multi-step reaction with 19 steps

1.1: triethylamine / tetrahydrofuran / -40 - 0 °C

2.1: 6.15 g / lithium chloride / tetrahydrofuran / 20 °C

3.1: sodium hexamethyldisilazide / tetrahydrofuran / 1.33 h / -78 °C

3.2: 69 percent / tetrahydrofuran / -78 - -40 °C

4.1: 74 percent / lithium borohydride / diethyl ether; H₂O / 1 h / 0 °C

5.1: 100 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 0 °C

6.1: 2.43 g / diethyl ether / -78 - 20 °C

7.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 0 °C

8.1: (+)-B-chlorodiisopinocampheylborane; triethylamine / diethyl ether / 1 h / 0 °C

8.2: diethyl ether / 37 h / -78 - -25 °C

8.3: 48 percent / aq. hydrogen peroxide / methanol; various solvent(s) / 1 h / 0 °C / pH 7.0

9.1: 91 percent / tetramethylammonium triacetoxyborohydride; acetic acid / acetonitrile / -25 - 0 °C

10.1: 97 percent / pyridium p-toluenesulfonate / acetone

11.1: 99 percent / TBAF / tetrahydrofuran / 20 °C

12.1: 81 percent / pyridine; DMAP / CH₂Cl₂ / 1 h / 20 °C

13.1: 97 percent / imidazole / dimethylformamide / 3 h / 50 °C

14.1: 90 percent / Dibal-H / CH₂Cl₂; toluene / 2 h / -78 °C

15.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 0 °C

16.1: 2-methyl-2-butene; sodium dihydrogen phosphate monohydrate; sodium chlorite / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 0.67 h / 20 °C

17.1: 60.4 mg / ethyl acetate; diethyl ether / 1 h / 20 °C

18.1: 71 percent / dimethylaluminium amide / CH₂Cl₂ / 39 h / Heating

19.1: 97 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

With pyridine; 1H-imidazole; dmap; sodium chlorite; sodium dihydrogenphosphate; lithium borohydride; pyridium para-toluenesulfonate; (+)-β-chlorodiisopinocampheylborane; 2-methyl-but-2-ene; oxalyl dichloride; dimethylaluminium amide; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; dimethyl sulfoxide; triethylamine; lithium chloride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol; 5.1: Swern oxiadtion / 7.1: Swern oxiadtion;

DOI:10.1021/ja020091v

upstream raw materials:

(2S,4S,5S,6S,7S,8S)-8-[(4S,6S)-2,2-Dimethyl-6-((S)-1-methyl-pent-4-ynyl)-[1,3]dioxan-4-yl]-2-ethyl-7-(4-methoxy-benzyloxy)-4,6-dimethyl-5-triethylsilanyloxy-nonanoic acid amide

O-(4-methoxybenzyl)-trichloroacetimidate

6-trimethylsilanyl-hex-5-yn-1-ol

6-(trimethylsilyl)hex-5-ynoic acid:

Downstream raw materials:

(2S,4S,6S,7S,8S)-8-[(4S,6S)-2,2-Dimethyl-6-((S)-1-methyl-pent-4-ynyl)-[1,3]dioxan-4-yl]-2-ethyl-7-(4-methoxy-benzyloxy)-4,6-dimethyl-5-oxo-nonanoic acid amide

(2S,3S,4S,5S,6R,9S,11S)-9-Ethyl-2-((2S,3S)-2-hydroxy-3-methyl-hept-6-ynyl)-4-(4-methoxy-benzyloxy)-3,5,11-trimethyl-1-oxa-7-aza-spiro[5.5]undecan-8-one