tert-Butyl-[(E)-(1R,3S,12S,13R)-7-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-13-(4-methoxy-benzyloxy)-2-oxa-tricyclo[8.3.0.0^1,3]trideca-6,10-diene-4,8-diyn-12-yloxy]-dimethyl-silane

Base Information

• Chemical Name: tert-Butyl-[(E)-(1R,3S,12S,13R)-7-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-13-(4-methoxy-benzyloxy)-2-oxa-tricyclo[8.3.0.0^1,3]trideca-6,10-diene-4,8-diyn-12-yloxy]-dimethyl-silane
• CAS No.: 189105-53-1
• Molecular Formula: C₃₁H₃₈O₆Si
• Molecular Weight: 534.725

Synonyms:

Chemical Property of tert-Butyl-[(E)-(1R,3S,12S,13R)-7-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-13-(4-methoxy-benzyloxy)-2-oxa-tricyclo[8.3.0.0^1,3]trideca-6,10-diene-4,8-diyn-12-yloxy]-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of tert-Butyl-[(E)-(1R,3S,12S,13R)-7-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-13-(4-methoxy-benzyloxy)-2-oxa-tricyclo[8.3.0.0^1,3]trideca-6,10-diene-4,8-diyn-12-yloxy]-dimethyl-silane

There total 19 articles about tert-Butyl-[(E)-(1R,3S,12S,13R)-7-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-13-(4-methoxy-benzyloxy)-2-oxa-tricyclo[8.3.0.0^1,3]trideca-6,10-diene-4,8-diyn-12-yloxy]-dimethyl-silane 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:

Methanesulfonic acid (1R,3S,7R,12S,13R)-12-(tert-butyl-dimethyl-silanyloxy)-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-13-(4-methoxy-benzyloxy)-2-oxa-tricyclo[8.3.0.01,3]tridec-10-ene-4,8-diyn-7-yl ester → tert-Butyl-[(E)-(1R,3S,12S,13R)-7-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-13-(4-methoxy-benzyloxy)-2-oxa-tricyclo[8.3.0.01,3]trideca-6,10-diene-4,8-diyn-12-yloxy]-dimethyl-silane (189105-53-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane-d2; Ambient temperature;

DOI:10.1055/s-1997-780

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → tert-Butyl-[(E)-(1R,3S,12S,13R)-7-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-13-(4-methoxy-benzyloxy)-2-oxa-tricyclo[8.3.0.01,3]trideca-6,10-diene-4,8-diyn-12-yloxy]-dimethyl-silane (189105-53-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 10-camphorsulfonic acid / CH₂Cl₂

2: imidazole / dimethylformamide / 60 °C

3: DIBAL / CH₂Cl₂ / -78 °C

4: 96 percent / Dess-Martin periodinane / CH₂Cl₂

5: 65 percent / LiHMDS, CeCl₃ / tetrahydrofuran / -20 deg C -> RT

6: 1.) MsCl, Et₃N, DMAP, 2.) Bu₄NF, 3.) TBSOTf, 2,6-lutidine / 1.) CH₂Cl₂, 2.) THF, 0 deg C, 1 h, 3.) THF, -78 deg C

7: Et₃N / CH₂Cl₂

8: DBU / CD₂Cl₂ / Ambient temperature

With 1H-imidazole; 2,6-dimethylpyridine; dmap; cerium(III) chloride; t-butyldimethylsiyl triflate; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; Dess-Martin periodane; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; dichloromethane-d2; N,N-dimethyl-formamide;

DOI:10.1055/s-1997-780

Reference yield:

(R)-4-((R)-1-Ethynyl-4-triethylsilanyl-1-triethylsilanyloxy-but-3-ynyl)-2,2-dimethyl-[1,3]dioxolane → tert-Butyl-[(E)-(1R,3S,12S,13R)-7-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-13-(4-methoxy-benzyloxy)-2-oxa-tricyclo[8.3.0.01,3]trideca-6,10-diene-4,8-diyn-12-yloxy]-dimethyl-silane (189105-53-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 84 percent / BuLi, CeCl₃ / tetrahydrofuran / -78 °C

2: 99 percent / pyridine

3: 1.) MsCl, DMAP, Et₃N, 2.) DBU / 1.) CH₂Cl₂, 2.) xylene, reflux, 30 min

4: 1.) DDQ, 2.) AgNO₃, 2,6-lutidine, 3.) K₂CO₃, 4.) pyridine

5: 10-camphorsulfonic acid / CH₂Cl₂

6: imidazole / dimethylformamide / 60 °C

7: DIBAL / CH₂Cl₂ / -78 °C

8: 96 percent / Dess-Martin periodinane / CH₂Cl₂

9: 65 percent / LiHMDS, CeCl₃ / tetrahydrofuran / -20 deg C -> RT

10: 1.) MsCl, Et₃N, DMAP, 2.) Bu₄NF, 3.) TBSOTf, 2,6-lutidine / 1.) CH₂Cl₂, 2.) THF, 0 deg C, 1 h, 3.) THF, -78 deg C

11: Et₃N / CH₂Cl₂

12: DBU / CD₂Cl₂ / Ambient temperature

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; n-butyllithium; cerium(III) chloride; t-butyldimethylsiyl triflate; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; silver nitrate; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; dichloromethane-d2; N,N-dimethyl-formamide;

DOI:10.1055/s-1997-780

upstream raw materials:

O-(4-methoxybenzyl)-trichloroacetimidate

(2R,3aR,6S,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-phenyl)-3a-hydroxymethyl-tetrahydro-cyclopenta[1,3]dioxol-4-one

(1R,3S,7R,12S,13R)-12-(tert-Butyl-dimethyl-silanyloxy)-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-13-(4-methoxy-benzyloxy)-2-oxa-tricyclo[8.3.0.0^1,3]tridec-10-ene-4,8-diyn-7-ol

2,2-Dimethyl-propionic acid (1R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-2-[(R)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-triethylsilanyloxy-hexa-1,5-diynyl]-1,5-dihydroxy-cyclopent-2-enylmethyl ester

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