(S)-17-(tert-Butyl-diphenyl-silanyloxy)-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-heptadecanoic acid

Base Information

Chemical Name:(S)-17-(tert-Butyl-diphenyl-silanyloxy)-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-heptadecanoic acid
CAS No.:404868-05-9
Molecular Formula:C₆₀H₈₀O₉Si
Molecular Weight:973.375
Hs Code.:

Synonyms:(S)-17-(tert-Butyl-diphenyl-silanyloxy)-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-heptadecanoic acid

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Chemical Property of (S)-17-(tert-Butyl-diphenyl-silanyloxy)-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-heptadecanoic acid

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Technology Process of (S)-17-(tert-Butyl-diphenyl-silanyloxy)-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-heptadecanoic acid

There total 11 articles about (S)-17-(tert-Butyl-diphenyl-silanyloxy)-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-heptadecanoic acid 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: 35.0%

: 404868-04-8
(S)-17-(tert-Butyl-diphenyl-silanyloxy)-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-heptadecanoic acid tert-butyl ester

: 404868-05-9
(S)-17-(tert-Butyl-diphenyl-silanyloxy)-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-heptadecanoic acid

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 10h;
DOI:10.1021/ja036521e

Reference yield:

: 106-02-5,81031-90-5
pentadecanolide

: 404868-05-9
(S)-17-(tert-Butyl-diphenyl-silanyloxy)-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-heptadecanoic acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: LDA / hexane; tetrahydrofuran / 1 h / -78 °C

1.2: 61 percent / hexane; tetrahydrofuran / 2 h / -40 °C

2.1: [RuCl₂(COD)]n; H₂; Et₃N / (S)-BINAP / methanol; tetrahydrofuran / 15 h / 70 °C / 11400 Torr

3.1: imidazole / dimethylformamide / 20 °C

4.1: 63 percent / TMSOTf / CH₂Cl₂; acetonitrile / 0.5 h / -50 °C

5.1: 83 percent / NH₃ / methanol

6.1: 35 percent / F₃CCO₂H / CH₂Cl₂ / 10 h / 20 °C

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; [RuCl₂(COD)]n; ammonia; hydrogen; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja036521e

Reference yield:

: 404867-95-4
17-hydroxy-3-oxo-heptadecanoic acid tert-butyl ester

: 404868-05-9
(S)-17-(tert-Butyl-diphenyl-silanyloxy)-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-heptadecanoic acid

Guidance literature:: Multi-step reaction with 5 steps

1: [RuCl₂(COD)]n; H₂; Et₃N / (S)-BINAP / methanol; tetrahydrofuran / 15 h / 70 °C / 11400 Torr

2: imidazole / dimethylformamide / 20 °C

3: 63 percent / TMSOTf / CH₂Cl₂; acetonitrile / 0.5 h / -50 °C

4: 83 percent / NH₃ / methanol

5: 35 percent / F₃CCO₂H / CH₂Cl₂ / 10 h / 20 °C

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; [RuCl₂(COD)]n; ammonia; hydrogen; triethylamine; trifluoroacetic acid; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja036521e