(3R,5R)-3-{(2S,13S)-2-(tert-Butyl-dimethyl-silanyloxy)-13-hydroxy-13-[(2S,5S,2'S,5'S)-5'-((R)-1-hydroxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-trideca-8,10-diynyl}-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one

Base Information

• Chemical Name: (3R,5R)-3-{(2S,13S)-2-(tert-Butyl-dimethyl-silanyloxy)-13-hydroxy-13-[(2S,5S,2'S,5'S)-5'-((R)-1-hydroxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-trideca-8,10-diynyl}-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one
• CAS No.: 152037-57-5
• Molecular Formula: C₄₉H₇₈O₇SSi
• Molecular Weight: 839.306
• Mol file: 152037-57-5.mol

Synonyms:

Chemical Property of (3R,5R)-3-{(2S,13S)-2-(tert-Butyl-dimethyl-silanyloxy)-13-hydroxy-13-[(2S,5S,2'S,5'S)-5'-((R)-1-hydroxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-trideca-8,10-diynyl}-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5R)-3-{(2S,13S)-2-(tert-Butyl-dimethyl-silanyloxy)-13-hydroxy-13-[(2S,5S,2'S,5'S)-5'-((R)-1-hydroxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-trideca-8,10-diynyl}-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one

There total 8 articles about (3R,5R)-3-{(2S,13S)-2-(tert-Butyl-dimethyl-silanyloxy)-13-hydroxy-13-[(2S,5S,2'S,5'S)-5'-((R)-1-hydroxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-trideca-8,10-diynyl}-5-methyl-3-phenylsulfanyl-dihydro-furan-2-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: 45.0%

(R)-1-[(2S,5S,2'S,5'S)-5'-((S)-1-Hydroxy-but-3-ynyl)-octahydro-[2,2']bifuranyl-5-yl]-undecan-1-ol + (3R,5R)-3-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-9-iodo-non-8-ynyl]-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one (152037-56-4) → (3R,5R)-3-{(2S,13S)-2-(tert-Butyl-dimethyl-silanyloxy)-13-hydroxy-13-[(2S,5S,2'S,5'S)-5'-((R)-1-hydroxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-trideca-8,10-diynyl}-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one (152037-57-5)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)60671-8

Reference yield:

dilithiated phenylthioacetic acid (115338-23-3) → (3R,5R)-3-{(2S,13S)-2-(tert-Butyl-dimethyl-silanyloxy)-13-hydroxy-13-[(2S,5S,2'S,5'S)-5'-((R)-1-hydroxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-trideca-8,10-diynyl}-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one (152037-57-5)

Guidance literature:

Multi-step reaction with 5 steps

3: K₂CO₃ / methanol

4: I₂, morpholine

5: 45 percent / Pd(Ph₃P)2Cl₂, CuI, i-Pr₂NH / tetrahydrofuran

With morpholine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; iodine; potassium carbonate; diisopropylamine; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4039(00)60671-8

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (3R,5R)-3-{(2S,13S)-2-(tert-Butyl-dimethyl-silanyloxy)-13-hydroxy-13-[(2S,5S,2'S,5'S)-5'-((R)-1-hydroxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-trideca-8,10-diynyl}-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one (152037-57-5)

Guidance literature:

Multi-step reaction with 5 steps

3: K₂CO₃ / methanol

4: I₂, morpholine

5: 45 percent / Pd(Ph₃P)2Cl₂, CuI, i-Pr₂NH / tetrahydrofuran

With morpholine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; iodine; potassium carbonate; diisopropylamine; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4039(00)60671-8

upstream raw materials:

(3R,5R)-3-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-9-iodo-non-8-ynyl]-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one

dilithiated phenylthioacetic acid

tert-butyldimethylsilyl chloride

(S)-Non-8-yne-1,2-diol