(4R,5S)-3-[(E)-(2R,3S,5R,6R,10S,12S,13R,14S,16R)-6-Allyl-16-[1,3]dithian-2-yl-3-hydroxy-12,14-dimethoxy-5-(4-methoxy-benzyloxy)-2,8,10-trimethyl-13-triisopropylsilanyloxy-heptadec-7-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one

Base Information

• Chemical Name: (4R,5S)-3-[(E)-(2R,3S,5R,6R,10S,12S,13R,14S,16R)-6-Allyl-16-[1,3]dithian-2-yl-3-hydroxy-12,14-dimethoxy-5-(4-methoxy-benzyloxy)-2,8,10-trimethyl-13-triisopropylsilanyloxy-heptadec-7-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one
• CAS No.: 137298-94-3
• Molecular Formula: C₅₆H₈₉NO₉S₂Si
• Molecular Weight: 1012.54
• Mol file: 137298-94-3.mol

Synonyms:

Chemical Property of (4R,5S)-3-[(E)-(2R,3S,5R,6R,10S,12S,13R,14S,16R)-6-Allyl-16-[1,3]dithian-2-yl-3-hydroxy-12,14-dimethoxy-5-(4-methoxy-benzyloxy)-2,8,10-trimethyl-13-triisopropylsilanyloxy-heptadec-7-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-3-[(E)-(2R,3S,5R,6R,10S,12S,13R,14S,16R)-6-Allyl-16-[1,3]dithian-2-yl-3-hydroxy-12,14-dimethoxy-5-(4-methoxy-benzyloxy)-2,8,10-trimethyl-13-triisopropylsilanyloxy-heptadec-7-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one

There total 9 articles about (4R,5S)-3-[(E)-(2R,3S,5R,6R,10S,12S,13R,14S,16R)-6-Allyl-16-[1,3]dithian-2-yl-3-hydroxy-12,14-dimethoxy-5-(4-methoxy-benzyloxy)-2,8,10-trimethyl-13-triisopropylsilanyloxy-heptadec-7-enoyl]-4-methyl-5-phenyl-oxazolidin-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: 87.0%

(4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one (77877-20-4) + (E)-(3R,4R,8S,10S,11R,12S,14R)-4-Allyl-14-[1,3]dithian-2-yl-10,12-dimethoxy-3-(4-methoxy-benzyloxy)-6,8-dimethyl-11-triisopropylsilanyloxy-pentadec-5-enal (137298-93-2) → (4R,5S)-3-[(E)-(2R,3S,5R,6R,10S,12S,13R,14S,16R)-6-Allyl-16-[1,3]dithian-2-yl-3-hydroxy-12,14-dimethoxy-5-(4-methoxy-benzyloxy)-2,8,10-trimethyl-13-triisopropylsilanyloxy-heptadec-7-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one (137298-94-3)

Guidance literature:

With di-n-butylboryl trifluoromethanesulfonate; triethylamine;

DOI:10.1016/S0040-4039(00)92267-6

Reference yield:

(5S,6R)-6-((1S,3R)-4-Benzyloxy-1-methoxy-3-methyl-butyl)-5-methoxy-tetrahydro-pyran-2-one (128461-50-7) → (4R,5S)-3-[(E)-(2R,3S,5R,6R,10S,12S,13R,14S,16R)-6-Allyl-16-[1,3]dithian-2-yl-3-hydroxy-12,14-dimethoxy-5-(4-methoxy-benzyloxy)-2,8,10-trimethyl-13-triisopropylsilanyloxy-heptadec-7-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one (137298-94-3)

Guidance literature:

Multi-step reaction with 9 steps

1: H₂ / Pd/C

2: Swern

3: BF₃*OEt₂

4: 70 percent / NaN(TMS)2 / tetrahydrofuran / -78 °C

5: 95 percent / LiAlH₄

8: 75 percent / 1,1-(azodicarbonyl)dipiperidine, MeMgI

9: 87 percent / n-Bu₂BOTf, N(Et)3

With lithium aluminium tetrahydride; methyl magnesium iodide; di-n-butylboryl trifluoromethanesulfonate; boron trifluoride diethyl etherate; hydrogen; sodium hexamethyldisilazane; triethylamine; 1,1'-azodicarbonyl-dipiperidine; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)92267-6

Reference yield:

(5S,6R)-6-((1S,3R)-4-Hydroxy-1-methoxy-3-methyl-butyl)-5-methoxy-tetrahydro-pyran-2-one → (4R,5S)-3-[(E)-(2R,3S,5R,6R,10S,12S,13R,14S,16R)-6-Allyl-16-[1,3]dithian-2-yl-3-hydroxy-12,14-dimethoxy-5-(4-methoxy-benzyloxy)-2,8,10-trimethyl-13-triisopropylsilanyloxy-heptadec-7-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one (137298-94-3)

Guidance literature:

Multi-step reaction with 8 steps

1: Swern

2: BF₃*OEt₂

3: 70 percent / NaN(TMS)2 / tetrahydrofuran / -78 °C

4: 95 percent / LiAlH₄

7: 75 percent / 1,1-(azodicarbonyl)dipiperidine, MeMgI

8: 87 percent / n-Bu₂BOTf, N(Et)3

With lithium aluminium tetrahydride; methyl magnesium iodide; di-n-butylboryl trifluoromethanesulfonate; boron trifluoride diethyl etherate; sodium hexamethyldisilazane; triethylamine; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)92267-6

upstream raw materials:

(4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one

(E)-(3R,4R,8S,10S,11R,12S,14R)-4-Allyl-14-[1,3]dithian-2-yl-10,12-dimethoxy-3-(4-methoxy-benzyloxy)-6,8-dimethyl-11-triisopropylsilanyloxy-pentadec-5-enal

(5S,6R)-6-((1S,3R)-4-Benzyloxy-1-methoxy-3-methyl-butyl)-5-methoxy-tetrahydro-pyran-2-one

(5S,6R)-6-((1S,3R)-3-[1,3]Dithian-2-yl-1-methoxy-butyl)-5-methoxy-tetrahydro-pyran-2-one

Downstream raw materials:

C₇₄H₁₃₈O₉S₂Si₃

C₇₄H₁₃₈O₉S₂Si₃

(E)-(2R,3S,5R,6R,10S,12S,13R,14S,16R)-6-Allyl-16-[1,3]dithian-2-yl-12,14-dimethoxy-5-(4-methoxy-benzyloxy)-2,8,10-trimethyl-3,13-bis-triisopropylsilanyloxy-heptadec-7-enal