(2R,4aR,6S,7R,9aS)-7-(tert-Butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-6-triethylsilanyloxymethyl-4a,6,7,9a-tetrahydro-4H-1,3,5-trioxa-benzocycloheptene

Base Information

• Chemical Name: (2R,4aR,6S,7R,9aS)-7-(tert-Butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-6-triethylsilanyloxymethyl-4a,6,7,9a-tetrahydro-4H-1,3,5-trioxa-benzocycloheptene
• CAS No.: 213815-40-8
• Molecular Formula: C₂₈H₄₈O₅Si₂
• Molecular Weight: 520.857
• Mol file: 213815-40-8.mol

Synonyms:(2R,4aR,6S,7R,9aS)-7-(tert-Butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-6-triethylsilanyloxymethyl-4a,6,7,9a-tetrahydro-4H-1,3,5-trioxa-benzocycloheptene

Chemical Property of (2R,4aR,6S,7R,9aS)-7-(tert-Butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-6-triethylsilanyloxymethyl-4a,6,7,9a-tetrahydro-4H-1,3,5-trioxa-benzocycloheptene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4aR,6S,7R,9aS)-7-(tert-Butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-6-triethylsilanyloxymethyl-4a,6,7,9a-tetrahydro-4H-1,3,5-trioxa-benzocycloheptene

There total 15 articles about (2R,4aR,6S,7R,9aS)-7-(tert-Butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-6-triethylsilanyloxymethyl-4a,6,7,9a-tetrahydro-4H-1,3,5-trioxa-benzocycloheptene 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: 99.0%

t-butyldimethylsiyl triflate (69739-34-0) + (2R,4aR,6S,7R,9aS)-7-Methyl-2-phenyl-6-triethylsilanyloxymethyl-4a,6,7,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-7-ol (213815-39-5) → (2R,4aR,6S,7R,9aS)-7-(tert-Butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-6-triethylsilanyloxymethyl-4a,6,7,9a-tetrahydro-4H-1,3,5-trioxa-benzocycloheptene (213815-40-8)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(98)01312-4

Reference yield:

[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-acetaldehyde (193970-21-7) → (2R,4aR,6S,7R,9aS)-7-(tert-Butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-6-triethylsilanyloxymethyl-4a,6,7,9a-tetrahydro-4H-1,3,5-trioxa-benzocycloheptene (213815-40-8)

Guidance literature:

Multi-step reaction with 14 steps

1: 80 percent / NaHMDS / tetrahydrofuran / -78 °C

2: 94 percent / 9-BBN / tetrahydrofuran / Ambient temperature

3: 97 percent / TBAF / tetrahydrofuran / Ambient temperature

4: 96 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

5: 98 percent / KH / tetrahydrofuran / 0 deg C -> RT

6: 1.) n-Bu₃SnCl, sec-BuLi, TMEDA, 2.) TBAF, 3.) SO₃*pyridine, DMSO, Et₃N, 4.) BF₃*OEt₂

7: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂/MeOH, -78 deg C, 2.) CH₂Cl₂/MeOH, -78 deg C -> RT

8: 95 percent / imidazole / dimethylformamide / 0 °C

9: 98 percent / (COCl)2, DMSO / CH₂Cl₂ / -78 °C

10: 1.) LiHMDS, 2.) PhSeCl, 3.) H₂O₂ / 1.) THF, -78 deg C, 2.) THF, -78 deg C -> RT, 3.) THF/H₂O, RT

11: 83 percent / toluene / -78 °C

12: 99 percent / TBAF / tetrahydrofuran / Ambient temperature

13: 99 percent / Et₃N / CH₂Cl₂ / Ambient temperature

14: 99 percent / 2,6-lutidine / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; Phenylselenyl chloride; oxalyl dichloride; pyridine-SO₃ complex; N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; tributyltin chloride; tetrabutyl ammonium fluoride; dihydrogen peroxide; sec.-butyllithium; sodium hexamethyldisilazane; potassium hydride; ozone; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(98)01312-4

Reference yield:

(2R,4S,5R)-4-(3-Hydroxy-propyl)-2-phenyl-[1,3]dioxan-5-ol (213815-26-0) → (2R,4aR,6S,7R,9aS)-7-(tert-Butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-6-triethylsilanyloxymethyl-4a,6,7,9a-tetrahydro-4H-1,3,5-trioxa-benzocycloheptene (213815-40-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 96 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

2: 98 percent / KH / tetrahydrofuran / 0 deg C -> RT

3: 1.) n-Bu₃SnCl, sec-BuLi, TMEDA, 2.) TBAF, 3.) SO₃*pyridine, DMSO, Et₃N, 4.) BF₃*OEt₂

4: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂/MeOH, -78 deg C, 2.) CH₂Cl₂/MeOH, -78 deg C -> RT

5: 95 percent / imidazole / dimethylformamide / 0 °C

6: 98 percent / (COCl)2, DMSO / CH₂Cl₂ / -78 °C

7: 1.) LiHMDS, 2.) PhSeCl, 3.) H₂O₂ / 1.) THF, -78 deg C, 2.) THF, -78 deg C -> RT, 3.) THF/H₂O, RT

8: 83 percent / toluene / -78 °C

9: 99 percent / TBAF / tetrahydrofuran / Ambient temperature

10: 99 percent / Et₃N / CH₂Cl₂ / Ambient temperature

11: 99 percent / 2,6-lutidine / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; Phenylselenyl chloride; oxalyl dichloride; pyridine-SO₃ complex; N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; tributyltin chloride; tetrabutyl ammonium fluoride; dihydrogen peroxide; sec.-butyllithium; potassium hydride; ozone; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(98)01312-4

upstream raw materials:

t-butyldimethylsiyl triflate

(2R,4aR,6S,7R,9aS)-7-Methyl-2-phenyl-6-triethylsilanyloxymethyl-4a,6,7,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-7-ol

[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-acetaldehyde

(2R,4S,5R)-4-(3-Hydroxy-propyl)-2-phenyl-[1,3]dioxan-5-ol

Downstream raw materials:

tert-Butyl-[(2R,4aR,6S,7R,9aS)-6-((1Z,3Z)-hepta-1,3,6-trienyl)-7-methyl-2-phenyl-4a,6,7,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-7-yloxy]-dimethyl-silane

tert-Butyl-[(2R,4aR,6S,7R,9aS)-6-(2,2-dibromo-vinyl)-7-methyl-2-phenyl-4a,6,7,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-7-yloxy]-dimethyl-silane

[(2R,4aR,6S,7R,9aS)-6-((Z)-2-Bromo-vinyl)-7-methyl-2-phenyl-4a,6,7,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-7-yloxy]-tert-butyl-dimethyl-silane

[(2R,4aR,6S,7R,9aS)-7-(tert-Butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-4a,6,7,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-6-yl]-methanol