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

Base Information

• Chemical Name: (S)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-(tert-butyl-diphenyl-silanyloxy)-heptadecanoic acid tert-butyl ester
• CAS No.: 404868-03-7
• Molecular Formula: C₆₆H₉₀O₁₀Si
• Molecular Weight: 1071.52
• Mol file: 404868-03-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (S)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-(tert-butyl-diphenyl-silanyloxy)-heptadecanoic acid tert-butyl ester 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: 63.0%

6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (125164-10-5) + 17-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-heptadecanoic acid tert-butyl ester (404868-12-8) → (S)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-(tert-butyl-diphenyl-silanyloxy)-heptadecanoic acid tert-butyl ester (404868-03-7) + (S)-3-((2S,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-(tert-butyl-diphenyl-silanyloxy)-heptadecanoic acid tert-butyl ester (404868-10-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; acetonitrile; at -50 ℃; for 0.5h;

DOI:10.1021/ja036521e

Reference yield:

pentadecanolide (106-02-5,81031-90-5) → (S)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-(tert-butyl-diphenyl-silanyloxy)-heptadecanoic acid tert-butyl ester (404868-03-7)

Guidance literature:

Multi-step reaction with 4 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

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; [RuCl₂(COD)]n; hydrogen; triethylamine; 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:

17-hydroxy-3-oxo-heptadecanoic acid tert-butyl ester (404867-95-4) → (S)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-(tert-butyl-diphenyl-silanyloxy)-heptadecanoic acid tert-butyl ester (404868-03-7)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1021/ja036521e

upstream raw materials:

6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

17-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-heptadecanoic acid tert-butyl ester

pentadecanolide

1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose

Downstream raw materials:

(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

(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