(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-nonan-1-ol

Base Information

• Chemical Name: (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-nonan-1-ol
• CAS No.: 382138-96-7
• Molecular Formula: C₃₉H₆₈O₆Si
• Molecular Weight: 661.051
• Mol file: 382138-96-7.mol

Synonyms:(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-nonan-1-ol

Chemical Property of (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-nonan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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-nonan-1-ol

There total 35 articles about (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-nonan-1-ol 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: 90.0%

2,2-Dimethyl-propionic acid (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-nonyl ester (382139-17-5) → (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-nonan-1-ol (382138-96-7)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 2h;

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,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-nonan-1-ol (382138-96-7)

Guidance literature:

Multi-step reaction with 15 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

With pyridine; 1H-imidazole; dmap; lithium borohydride; pyridium para-toluenesulfonate; (+)-β-chlorodiisopinocampheylborane; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; lithium chloride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 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,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-nonan-1-ol (382138-96-7)

Guidance literature:

Multi-step reaction with 14 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

With pyridine; 1H-imidazole; dmap; lithium borohydride; pyridium para-toluenesulfonate; (+)-β-chlorodiisopinocampheylborane; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; lithium chloride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 5.1: Swern oxiadtion / 7.1: Swern oxiadtion;

DOI:10.1021/ja020091v

upstream raw materials:

2,2-Dimethyl-propionic acid (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-nonyl ester

O-(4-methoxybenzyl)-trichloroacetimidate

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

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

Downstream raw materials:

(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

(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,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

(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