(5S,6S,8S,9S,10S,11S,12S,13S,15S)-15-(tert-Butyl-diphenyl-silanyloxymethyl)-10-(4-methoxy-benzyloxy)-5,9,11,13-tetramethyl-12-triethylsilanyloxy-1-trimethylsilanyl-heptadec-1-yne-6,8-diol

Base Information

• Chemical Name: (5S,6S,8S,9S,10S,11S,12S,13S,15S)-15-(tert-Butyl-diphenyl-silanyloxymethyl)-10-(4-methoxy-benzyloxy)-5,9,11,13-tetramethyl-12-triethylsilanyloxy-1-trimethylsilanyl-heptadec-1-yne-6,8-diol
• CAS No.: 382139-15-3
• Molecular Formula: C₅₅H₉₀O₆Si₃
• Molecular Weight: 931.572
• Mol file: 382139-15-3.mol

Synonyms:(5S,6S,8S,9S,10S,11S,12S,13S,15S)-15-(tert-Butyl-diphenyl-silanyloxymethyl)-10-(4-methoxy-benzyloxy)-5,9,11,13-tetramethyl-12-triethylsilanyloxy-1-trimethylsilanyl-heptadec-1-yne-6,8-diol

Chemical Property of (5S,6S,8S,9S,10S,11S,12S,13S,15S)-15-(tert-Butyl-diphenyl-silanyloxymethyl)-10-(4-methoxy-benzyloxy)-5,9,11,13-tetramethyl-12-triethylsilanyloxy-1-trimethylsilanyl-heptadec-1-yne-6,8-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6S,8S,9S,10S,11S,12S,13S,15S)-15-(tert-Butyl-diphenyl-silanyloxymethyl)-10-(4-methoxy-benzyloxy)-5,9,11,13-tetramethyl-12-triethylsilanyloxy-1-trimethylsilanyl-heptadec-1-yne-6,8-diol

There total 30 articles about (5S,6S,8S,9S,10S,11S,12S,13S,15S)-15-(tert-Butyl-diphenyl-silanyloxymethyl)-10-(4-methoxy-benzyloxy)-5,9,11,13-tetramethyl-12-triethylsilanyloxy-1-trimethylsilanyl-heptadec-1-yne-6,8-diol 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: 91.0%

(5S,8S,9S,10S,11S,12S,13S,15S)-15-(tert-Butyl-diphenyl-silanyloxymethyl)-8-hydroxy-10-(4-methoxy-benzyloxy)-5,9,11,13-tetramethyl-12-triethylsilanyloxy-1-trimethylsilanyl-heptadec-1-yn-6-one (382138-93-4) → (5S,6S,8S,9S,10S,11S,12S,13S,15S)-15-(tert-Butyl-diphenyl-silanyloxymethyl)-10-(4-methoxy-benzyloxy)-5,9,11,13-tetramethyl-12-triethylsilanyloxy-1-trimethylsilanyl-heptadec-1-yne-6,8-diol (382139-15-3)

Guidance literature:

With acetic acid; tetramethylammonium triacetoxyborohydride; In acetonitrile; at -25 - 0 ℃;

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) → (5S,6S,8S,9S,10S,11S,12S,13S,15S)-15-(tert-Butyl-diphenyl-silanyloxymethyl)-10-(4-methoxy-benzyloxy)-5,9,11,13-tetramethyl-12-triethylsilanyloxy-1-trimethylsilanyl-heptadec-1-yne-6,8-diol (382139-15-3)

Guidance literature:

Multi-step reaction with 10 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

With lithium borohydride; (+)-β-chlorodiisopinocampheylborane; oxalyl dichloride; sodium hexamethyldisilazane; acetic acid; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; lithium chloride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 6.1: Swern oxiadtion / 8.1: Swern oxiadtion;

DOI:10.1021/ja020091v

Reference yield:

6-(trimethylsilyl)hex-5-ynoic acid: (101224-43-5) → (5S,6S,8S,9S,10S,11S,12S,13S,15S)-15-(tert-Butyl-diphenyl-silanyloxymethyl)-10-(4-methoxy-benzyloxy)-5,9,11,13-tetramethyl-12-triethylsilanyloxy-1-trimethylsilanyl-heptadec-1-yne-6,8-diol (382139-15-3)

Guidance literature:

Multi-step reaction with 9 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

With lithium borohydride; (+)-β-chlorodiisopinocampheylborane; oxalyl dichloride; sodium hexamethyldisilazane; acetic acid; dimethyl sulfoxide; triethylamine; lithium chloride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetonitrile; 5.1: Swern oxiadtion / 7.1: Swern oxiadtion;

DOI:10.1021/ja020091v

upstream raw materials:

(5S,8S,9S,10S,11S,12S,13S,15S)-15-(tert-Butyl-diphenyl-silanyloxymethyl)-8-hydroxy-10-(4-methoxy-benzyloxy)-5,9,11,13-tetramethyl-12-triethylsilanyloxy-1-trimethylsilanyl-heptadec-1-yn-6-one

O-(4-methoxybenzyl)-trichloroacetimidate

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

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

Downstream raw materials:

(4S,6S)-4-[(1S,2S,3S,4S,5S,7S)-7-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-1,3,5-trimethyl-4-triethylsilanyloxy-nonyl]-2,2-dimethyl-6-((S)-1-methyl-5-trimethylsilanyl-pent-4-ynyl)-[1,3]dioxane

(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,5S,6R,7R,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-nonane-1,5-diol

(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