(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

Base Information

• Chemical Name: (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
• CAS No.: 189105-52-0
• Molecular Formula: C₃₁H₄₀O₇Si
• Molecular Weight: 552.74

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 17 articles about (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 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:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (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-ol (189105-52-0)

Guidance literature:

Multi-step reaction with 6 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

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; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; 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 → (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-ol (189105-52-0)

Guidance literature:

Multi-step reaction with 10 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

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; N,N-dimethyl-formamide;

DOI:10.1055/s-1997-780

Reference yield:

(S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-iodo-cyclopent-2-enol → (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-ol (189105-52-0)

Guidance literature:

Multi-step reaction with 14 steps

1: 1.) Et₃N, PdCl₂(PPh₃)2, 2.) DIBAL, 3.) pyridine / 1.) MeOH, 60 deg C, 2.) CH₂Cl₂, -78 deg C

2: 87 percent / OsO₄, MNO / acetone; H₂O

3: 1.) TsOH, 2.) K₂CO₃ / 1.) benzene, reflux, 30 min, 2.) MeOH

4: 1.) Bu₂SnO, 2.) NBS / 2.) toluene, reflux,, 2.) CHCl₃

5: 84 percent / BuLi, CeCl₃ / tetrahydrofuran / -78 °C

6: 99 percent / pyridine

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

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

9: 10-camphorsulfonic acid / CH₂Cl₂

10: imidazole / dimethylformamide / 60 °C

11: DIBAL / CH₂Cl₂ / -78 °C

12: 96 percent / Dess-Martin periodinane / CH₂Cl₂

13: 65 percent / LiHMDS, CeCl₃ / tetrahydrofuran / -20 deg C -> RT

14: 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

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; bis-triphenylphosphine-palladium(II) chloride; N-Bromosuccinimide; osmium(VIII) oxide; n-butyllithium; cerium(III) chloride; t-butyldimethylsiyl triflate; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; manganese(II) oxide; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; 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; water; N,N-dimethyl-formamide; acetone;

DOI:10.1055/s-1997-780

upstream raw materials:

C₄₃H₇₀O₈Si₃

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

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

Downstream raw materials:

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

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