(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

Base Information

• Chemical Name: (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
• CAS No.: 382138-93-4
• Molecular Formula: C₅₅H₈₈O₆Si₃
• Molecular Weight: 929.557
• Mol file: 382138-93-4.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 29 articles about (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 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: 48.0%

(S)-5-methyl-6-oxo-1-trimethylsilyl-hept-1-yne (382138-92-3) + (2R,3R,4S,5S,6S,8S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxy-decanal (382138-91-2) → (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)

Guidance literature:

(2R,3R,4S,5S,6S,8S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxy-decanal; With (+)-β-chlorodiisopinocampheylborane; triethylamine; In diethyl ether; at 0 ℃;

(S)-5-methyl-6-oxo-1-trimethylsilyl-hept-1-yne; In diethyl ether; at -78 - -20 ℃; for 36h;

With dihydrogen peroxide; In methanol; at 0 ℃; pH=7.0;

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,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)

Guidance literature:

Multi-step reaction with 9 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

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

DOI:10.1021/ja020091v

Reference yield:

6-(trimethylsilyl)hex-5-ynoic acid: (101224-43-5) → (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)

Guidance literature:

Multi-step reaction with 8 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

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

DOI:10.1021/ja020091v

upstream raw materials:

(S)-5-methyl-6-oxo-1-trimethylsilyl-hept-1-yne

(2R,3R,4S,5S,6S,8S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxy-decanal

O-(4-methoxybenzyl)-trichloroacetimidate

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

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,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

(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