(2S,4R,5S,6S,8S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-1-(4-methoxy-benzyloxy)-2,4,6-trimethyl-decan-3-one

Base Information

• Chemical Name: (2S,4R,5S,6S,8S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-1-(4-methoxy-benzyloxy)-2,4,6-trimethyl-decan-3-one
• CAS No.: 382138-88-7
• Molecular Formula: C₃₈H₅₄O₅Si
• Molecular Weight: 618.929
• Mol file: 382138-88-7.mol

Synonyms:(2S,4R,5S,6S,8S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-1-(4-methoxy-benzyloxy)-2,4,6-trimethyl-decan-3-one

Chemical Property of (2S,4R,5S,6S,8S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-1-(4-methoxy-benzyloxy)-2,4,6-trimethyl-decan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R,5S,6S,8S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-1-(4-methoxy-benzyloxy)-2,4,6-trimethyl-decan-3-one

There total 13 articles about (2S,4R,5S,6S,8S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-1-(4-methoxy-benzyloxy)-2,4,6-trimethyl-decan-3-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: 73.0%

(S)-1-(p-methoxybenzyloxy)-2-methylpentan-3-one (182193-69-7) + (2S,4S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-hexanal (253143-33-8) → (2S,4R,5S,6S,8S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-1-(4-methoxy-benzyloxy)-2,4,6-trimethyl-decan-3-one (382138-88-7)

Guidance literature:

With tin(II) trifluoromethanesulfonate; triethylamine; In dichloromethane; at -78 ℃; for 5h;

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

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (2S,4R,5S,6S,8S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-1-(4-methoxy-benzyloxy)-2,4,6-trimethyl-decan-3-one (382138-88-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triflic acid

2.1: triethylamine; tin(II) triflate / CH₂Cl₂ / 2 h / -78 °C

2.2: 2.30 g / CH₂Cl₂ / 5 h / -78 °C

With tin(II) trifluoromethanesulfonate; trifluorormethanesulfonic acid; triethylamine; In dichloromethane;

DOI:10.1021/ja020091v

Reference yield:

(2S)-2-ethyl-4-penten-1-ol (121074-21-3) → (2S,4R,5S,6S,8S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-1-(4-methoxy-benzyloxy)-2,4,6-trimethyl-decan-3-one (382138-88-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 20.6 g / imidazole; 4 Angstroem molecular sieves / petroleum ether; diethyl ether; dimethylformamide / 20 °C

2.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C

2.2: 92 percent / sodium hydroxide; hydroden peroxide / tetrahydrofuran; H₂O / 0 - 20 °C

3.1: pyridinium dichromate / CH₂Cl₂ / 0.5 h

4.1: 6.9 g / sodium chlorite; sulfamic acid / tetrahydrofuran; H₂O / 0 - 20 °C

5.1: triethylamine / tetrahydrofuran / -78 - 0 °C

6.1: 5.53 g / lithium chloride / tetrahydrofuran / 20 °C

7.1: sodium hexamethyldisilazide / tetrahydrofuran / 1 h / -78 °C

7.2: 95 percent / tetrahydrofuran / -78 - -40 °C

8.1: 90 percent / lithium borohydride / diethyl ether / 0.5 h / 0 °C

9.1: 100 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - -20 °C

10.1: triethylamine; tin(II) triflate / CH₂Cl₂ / 2 h / -78 °C

10.2: 2.30 g / CH₂Cl₂ / 5 h / -78 °C

With 1H-imidazole; sodium chlorite; dipyridinium dichromate; lithium borohydride; tin(II) trifluoromethanesulfonate; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; 4 A molecular sieve; aminosulfonic acid; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; lithium chloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; Petroleum ether; 9.1: Swern oxidation;

DOI:10.1021/ja020091v

upstream raw materials:

(S)-1-(p-methoxybenzyloxy)-2-methylpentan-3-one

(2S,4S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-hexanal

O-(4-methoxybenzyl)-trichloroacetimidate

(2S)-2-ethyl-4-penten-1-ol

Downstream raw materials:

(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

(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

(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

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