(5S,6S,9S,16S)-6-benzyloxy-5-(2-(benzyloxy)ethyl)-3,3-diethyl-14-hydroxy-9,20,20-trimethyl-19,19-diphenyl-16-triethylsilyloxy-4,18-dioxa-3,19-disilahenicos-12-yn-8-one

Base Information

• Chemical Name: (5S,6S,9S,16S)-6-benzyloxy-5-(2-(benzyloxy)ethyl)-3,3-diethyl-14-hydroxy-9,20,20-trimethyl-19,19-diphenyl-16-triethylsilyloxy-4,18-dioxa-3,19-disilahenicos-12-yn-8-one
• CAS No.: 905589-56-2
• Molecular Formula: C₅₈H₈₆O₇Si₃
• Molecular Weight: 979.573

Synonyms:(5S,6S,9S,16S)-6-benzyloxy-5-(2-(benzyloxy)ethyl)-3,3-diethyl-14-hydroxy-9,20,20-trimethyl-19,19-diphenyl-16-triethylsilyloxy-4,18-dioxa-3,19-disilahenicos-12-yn-8-one

Chemical Property of (5S,6S,9S,16S)-6-benzyloxy-5-(2-(benzyloxy)ethyl)-3,3-diethyl-14-hydroxy-9,20,20-trimethyl-19,19-diphenyl-16-triethylsilyloxy-4,18-dioxa-3,19-disilahenicos-12-yn-8-one

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Technology Process of (5S,6S,9S,16S)-6-benzyloxy-5-(2-(benzyloxy)ethyl)-3,3-diethyl-14-hydroxy-9,20,20-trimethyl-19,19-diphenyl-16-triethylsilyloxy-4,18-dioxa-3,19-disilahenicos-12-yn-8-one

There total 9 articles about (5S,6S,9S,16S)-6-benzyloxy-5-(2-(benzyloxy)ethyl)-3,3-diethyl-14-hydroxy-9,20,20-trimethyl-19,19-diphenyl-16-triethylsilyloxy-4,18-dioxa-3,19-disilahenicos-12-yn-8-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: 75.0%

(5S,8S,9S)-8,11-Bis-benzyloxy-1-iodo-5-methyl-9-triethylsilanyloxy-undec-1-yn-6-one (905589-35-7) + (3S)-4-(tert-butyldiphenylsilyl)oxy-3-(triethylsilyl)oxy-butyraldehyde (905589-27-7) → (5S,6S,9S,16S)-6-benzyloxy-5-(2-(benzyloxy)ethyl)-3,3-diethyl-14-hydroxy-9,20,20-trimethyl-19,19-diphenyl-16-triethylsilyloxy-4,18-dioxa-3,19-disilahenicos-12-yn-8-one (905589-56-2)

Guidance literature:

With chromium dichloride; nickel dichloride; In tetrahydrofuran; for 12h;

DOI:10.1021/ol0609457

Reference yield:

(2S)-4-benzyloxy-2-(4-methoxybenzyloxy)-butyraldehyde → (5S,6S,9S,16S)-6-benzyloxy-5-(2-(benzyloxy)ethyl)-3,3-diethyl-14-hydroxy-9,20,20-trimethyl-19,19-diphenyl-16-triethylsilyloxy-4,18-dioxa-3,19-disilahenicos-12-yn-8-one (905589-56-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 91 percent / MgBr₂*Et₂O / CH₂Cl₂ / 2 h / -78 °C

2: 112 mg / trifluoromethanesulfonic acid / CH₂Cl₂ / 20 °C

3: 72.6 mg / phosphate buffer; DDQ / CH₂Cl₂ / 2 h / 0 °C / pH 7

4: 65.2 mg / 2,6-lutidine / CH₂Cl₂ / 1 h / -40 °C

5: 89 percent / silver trifluoroacetate; N-iodosuccinimide / acetone / 0.5 h

6: 75 percent / CrCl₂*NiCl₂ / tetrahydrofuran / 12 h

With 2,6-dimethylpyridine; chromium dichloride; N-iodo-succinimide; phosphate buffer; trifluorormethanesulfonic acid; silver trifluoroacetate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; magnesium bromide; nickel dichloride; In tetrahydrofuran; dichloromethane; acetone; 1: Mikaiyama aldol reaction;

DOI:10.1021/ol0609457

Reference yield:

(S)-trimethyl(5-methyl-6-(trimethylsilyloxy)hept-6-en-1-ynyl)silane (905589-53-9) → (5S,6S,9S,16S)-6-benzyloxy-5-(2-(benzyloxy)ethyl)-3,3-diethyl-14-hydroxy-9,20,20-trimethyl-19,19-diphenyl-16-triethylsilyloxy-4,18-dioxa-3,19-disilahenicos-12-yn-8-one (905589-56-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 91 percent / MgBr₂*Et₂O / CH₂Cl₂ / 2 h / -78 °C

2: 112 mg / trifluoromethanesulfonic acid / CH₂Cl₂ / 20 °C

3: 72.6 mg / phosphate buffer; DDQ / CH₂Cl₂ / 2 h / 0 °C / pH 7

4: 65.2 mg / 2,6-lutidine / CH₂Cl₂ / 1 h / -40 °C

5: 89 percent / silver trifluoroacetate; N-iodosuccinimide / acetone / 0.5 h

6: 75 percent / CrCl₂*NiCl₂ / tetrahydrofuran / 12 h

With 2,6-dimethylpyridine; chromium dichloride; N-iodo-succinimide; phosphate buffer; trifluorormethanesulfonic acid; silver trifluoroacetate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; magnesium bromide; nickel dichloride; In tetrahydrofuran; dichloromethane; acetone; 1: Mikaiyama aldol reaction;

DOI:10.1021/ol0609457

upstream raw materials:

(5S,8S,9S)-8,11-Bis-benzyloxy-1-iodo-5-methyl-9-triethylsilanyloxy-undec-1-yn-6-one

(3S)-4-(tert-butyldiphenylsilyl)oxy-3-(triethylsilyl)oxy-butyraldehyde

(S)-trimethyl(5-methyl-6-(trimethylsilyloxy)hept-6-en-1-ynyl)silane

(5S,8S,9S)-8,11-Bis-benzyloxy-9-hydroxy-5-methyl-1-trimethylsilanyl-undec-1-yn-6-one

Downstream raw materials:

(2S,9S,12S,13S)-12,15-Bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-9-methyl-2,13-bis-triethylsilanyloxy-pentadec-5-yne-4,10-dione

(S)-1-[(2S,3S,5R,10S)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-10-methyl-1,6-dioxa-spiro[4.5]dec-(7Z)-ylidene]-5-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-pentan-2-one

(2S,3S,5R,7R,9S,15S)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-9-(tert-butyl-diphenyl-silanyloxymethyl)-15-methyl-1,6,8-trioxa-dispiro[4.1.5.3]pentadecan-11-one

(2S,9S,12S,13S)-12,15-Bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-2,13-dihydroxy-9-methyl-pentadec-5-yne-4,10-dione

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