(3S,5S)-5-((R)-2-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-1,3-dimethyl-3-trimethylsilanyloxy-pyrrolidin-2-one

Base Information

• Chemical Name: (3S,5S)-5-((R)-2-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-1,3-dimethyl-3-trimethylsilanyloxy-pyrrolidin-2-one
• CAS No.: 631416-71-2
• Molecular Formula: C₄₃H₇₉NO₄Si₃
• Molecular Weight: 758.361
• Mol file: 631416-71-2.mol

Synonyms:(3S,5S)-5-((R)-2-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-1,3-dimethyl-3-trimethylsilanyloxy-pyrrolidin-2-one

Chemical Property of (3S,5S)-5-((R)-2-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-1,3-dimethyl-3-trimethylsilanyloxy-pyrrolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5S)-5-((R)-2-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-1,3-dimethyl-3-trimethylsilanyloxy-pyrrolidin-2-one

There total 18 articles about (3S,5S)-5-((R)-2-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-1,3-dimethyl-3-trimethylsilanyloxy-pyrrolidin-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: 62.0%

(3S,5R)-3,5-bis(t-butyldimethylsilyloxy)octa-1-en-7-yne (161055-41-0) + (3S,5S)-5-((R)-2-{(1R,3aR,7aR)-4-[1-Bromo-meth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-1,3-dimethyl-3-trimethylsilanyloxy-pyrrolidin-2-one (631416-66-5) → (3S,5S)-5-((R)-2-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-1,3-dimethyl-3-trimethylsilanyloxy-pyrrolidin-2-one (631416-71-2)

Guidance literature:

With Pd₂(dibenzylideneacetone)2*CHCl₃; triethylamine; triphenylphosphine; In toluene; at 110 ℃; for 4h;

DOI:10.3390/80600488

Reference yield:

Calciferol (50-14-6) → (3S,5S)-5-((R)-2-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-1,3-dimethyl-3-trimethylsilanyloxy-pyrrolidin-2-one (631416-71-2)

Guidance literature:

Multi-step reaction with 13 steps

1.1: O₃ / CH₂Cl₂ / -78 °C

1.2: 90 percent / NaBH₄ / methanol / 0 °C

2.1: DMAP / CH₂Cl₂ / 0 °C

3.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

4.1: DMSO / 90 °C

5.1: DIBAL-H / CH₂Cl₂ / 0 °C

6.1: Et₃N / CH₂Cl₂

7.1: 26 percent / toluene / 110 °C

8.1: p-TsOH / methanol

9.1: H₂ / Pd/C

10.1: TPAP; NMO; molecular sieves 4A / CH₂Cl₂

11.1: CH₂Cl₂

12.1: LiHMDS / toluene / -78 °C

13.1: 62 percent / Pd₂(dba)3CHCl₃; Et₃N / 100 °C

With 2,6-dimethylpyridine; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In methanol; dichloromethane; toluene; 12.1: Wittig reaction;

DOI:10.1016/j.bmcl.2004.02.076

Reference yield:

(S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate (66774-80-9,111924-49-3) → (3S,5S)-5-((R)-2-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-1,3-dimethyl-3-trimethylsilanyloxy-pyrrolidin-2-one (631416-71-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 2,6-lutidine / CH₂Cl₂ / 0 °C

2: DMSO / 90 °C

3: DIBAL-H / CH₂Cl₂ / 0 °C

4: Et₃N / CH₂Cl₂

5: 26 percent / toluene / 110 °C

6: p-TsOH / methanol

7: H₂ / Pd/C

8: TPAP; NMO; molecular sieves 4A / CH₂Cl₂

9: CH₂Cl₂

10: LiHMDS / toluene / -78 °C

11: 62 percent / Pd₂(dba)3CHCl₃; Et₃N / 100 °C

With 2,6-dimethylpyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In methanol; dichloromethane; toluene; 10: Wittig reaction;

DOI:10.1016/j.bmcl.2004.02.076

upstream raw materials:

(3S,5R)-3,5-bis(t-butyldimethylsilyloxy)octa-1-en-7-yne

(3S,5S)-5-((R)-2-{(1R,3aR,7aR)-4-[1-Bromo-meth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-1,3-dimethyl-3-trimethylsilanyloxy-pyrrolidin-2-one

Calciferol

(S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate