4-[(17R,19R,24S,25R)-17,19-dihydroxy-25-methoxy-24-methylheptacos-1-ynyl]phenyl 3,4-di-O-benzyl-2-O-methyl-α-L-rhamnopyranoside

Base Information

Chemical Name:4-[(17R,19R,24S,25R)-17,19-dihydroxy-25-methoxy-24-methylheptacos-1-ynyl]phenyl 3,4-di-O-benzyl-2-O-methyl-α-L-rhamnopyranoside
CAS No.:1449576-22-0
Molecular Formula:C₅₆H₈₄O₈
Molecular Weight:885.278
Hs Code.:

Synonyms:4-[(17R,19R,24S,25R)-17,19-dihydroxy-25-methoxy-24-methylheptacos-1-ynyl]phenyl 3,4-di-O-benzyl-2-O-methyl-α-L-rhamnopyranoside

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Chemical Property of 4-[(17R,19R,24S,25R)-17,19-dihydroxy-25-methoxy-24-methylheptacos-1-ynyl]phenyl 3,4-di-O-benzyl-2-O-methyl-α-L-rhamnopyranoside

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Technology Process of 4-[(17R,19R,24S,25R)-17,19-dihydroxy-25-methoxy-24-methylheptacos-1-ynyl]phenyl 3,4-di-O-benzyl-2-O-methyl-α-L-rhamnopyranoside

There total 25 articles about 4-[(17R,19R,24S,25R)-17,19-dihydroxy-25-methoxy-24-methylheptacos-1-ynyl]phenyl 3,4-di-O-benzyl-2-O-methyl-α-L-rhamnopyranoside 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: 91.0%

: 1425471-39-1
(3R,4S,9R,11R)-3-methoxy-4-methylheptacos-26-yne-9,11-diol

: 1449576-21-9
p-iodophenyl 3,4-di-O-benzyl-2-O-methyl-α-L-rhamnopyranoside

: 1449576-22-0
4-[(17R,19R,24S,25R)-17,19-dihydroxy-25-methoxy-24-methylheptacos-1-ynyl]phenyl 3,4-di-O-benzyl-2-O-methyl-α-L-rhamnopyranoside

Guidance literature:: With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; at 40 ℃; for 5h;
DOI:10.1002/ejoc.201300437

Reference yield:

: 1040731-61-0
(8R)-ethyl-(7S)-methyloxocan-2-one

: 1449576-22-0
4-[(17R,19R,24S,25R)-17,19-dihydroxy-25-methoxy-24-methylheptacos-1-ynyl]phenyl 3,4-di-O-benzyl-2-O-methyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 10 steps

1.1: potassium carbonate / 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide / 20 °C

3.1: diisobutylaluminium hydride / dichloromethane; diethyl ether / -84 °C / Inert atmosphere

4.1: niobium pentachloride / dichloromethane / 0.08 h / Inert atmosphere

4.2: 2 h / Inert atmosphere

5.1: (R)-[{RuCl(tol-BINAP)}₂(μ-Cl)₃][NH₂Me₂]; hydrogen / ethanol / 20 °C / 15001.5 Torr / Inert atmosphere; Autoclave

6.1: trimethylaluminum / tetrahydrofuran; toluene / 0 - 20 °C

6.2: 0 °C

7.1: tert.-butyl lithium / diethyl ether / 1 h / -84 °C

7.2: 1 h

8.1: tetramethylammonium triacetoxyborohydride; acetic acid / tetrahydrofuran; acetonitrile / 6 h / -25 °C

9.1: potassium carbonate; methanol / 20 °C

10.1: triphenylphosphine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / 5 h / 40 °C

With methanol; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; (R)-[{RuCl(tol-BINAP)}₂(μ-Cl)₃][NH₂Me₂]; hydrogen; trimethylaluminum; tert.-butyl lithium; niobium pentachloride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 10.1: |Sonogashira Cross-Coupling;
DOI:10.1002/ejoc.201300437

Reference yield:

: 1040731-63-2
(7R)-methoxy-(6S)-methylnonanoic acid methyl ester

: 1449576-22-0
4-[(17R,19R,24S,25R)-17,19-dihydroxy-25-methoxy-24-methylheptacos-1-ynyl]phenyl 3,4-di-O-benzyl-2-O-methyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: diisobutylaluminium hydride / dichloromethane; diethyl ether / -84 °C / Inert atmosphere

2.1: niobium pentachloride / dichloromethane / 0.08 h / Inert atmosphere

2.2: 2 h / Inert atmosphere

3.1: (R)-[{RuCl(tol-BINAP)}₂(μ-Cl)₃][NH₂Me₂]; hydrogen / ethanol / 20 °C / 15001.5 Torr / Inert atmosphere; Autoclave

4.1: trimethylaluminum / tetrahydrofuran; toluene / 0 - 20 °C

4.2: 0 °C

5.1: tert.-butyl lithium / diethyl ether / 1 h / -84 °C

5.2: 1 h

6.1: tetramethylammonium triacetoxyborohydride; acetic acid / tetrahydrofuran; acetonitrile / 6 h / -25 °C

7.1: potassium carbonate; methanol / 20 °C

8.1: triphenylphosphine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / 5 h / 40 °C

With methanol; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; (R)-[{RuCl(tol-BINAP)}₂(μ-Cl)₃][NH₂Me₂]; hydrogen; trimethylaluminum; tert.-butyl lithium; niobium pentachloride; diisobutylaluminium hydride; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; toluene; acetonitrile; 8.1: |Sonogashira Cross-Coupling;
DOI:10.1002/ejoc.201300437