(2S,3S,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-6-[(S)-2-((1S,2S)-2-methyl-cyclopropyl)-2-triethylsilanyloxy-ethyl]-2-vinyl-tetrahydro-pyran

Base Information

• Chemical Name: (2S,3S,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-6-[(S)-2-((1S,2S)-2-methyl-cyclopropyl)-2-triethylsilanyloxy-ethyl]-2-vinyl-tetrahydro-pyran
• CAS No.: 884338-32-3
• Molecular Formula: C₃₆H₅₆O₃Si₂
• Molecular Weight: 593.01
• Mol file: 884338-32-3.mol

Synonyms:

Chemical Property of (2S,3S,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-6-[(S)-2-((1S,2S)-2-methyl-cyclopropyl)-2-triethylsilanyloxy-ethyl]-2-vinyl-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-6-[(S)-2-((1S,2S)-2-methyl-cyclopropyl)-2-triethylsilanyloxy-ethyl]-2-vinyl-tetrahydro-pyran

There total 18 articles about (2S,3S,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-6-[(S)-2-((1S,2S)-2-methyl-cyclopropyl)-2-triethylsilanyloxy-ethyl]-2-vinyl-tetrahydro-pyran 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:

(E)-4-((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-but-2-en-1-ol (884338-24-3) → (2S,3S,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-6-[(S)-2-((1S,2S)-2-methyl-cyclopropyl)-2-triethylsilanyloxy-ethyl]-2-vinyl-tetrahydro-pyran (884338-32-3)

Guidance literature:

Multi-step reaction with 18 steps

1.1: D-(-)-DIPT; Ti(O-iPr)4; TBHP / CH₂Cl₂ / 3 h / -20 °C

1.2: 92 percent / Red-Al / tetrahydrofuran / 3 h / -10 °C

2.1: Et₃N; DMAP / dimethylformamide / 5 h / 0 - 20 °C

3.1: Et₃N; DMAP / CH₂Cl₂ / 0.5 h / 0 - 20 °C

4.1: CSA / methanol / 48 h / 20 °C

5.1: imidazole; DMAP / dimethylformamide / 24 h / 0 - 20 °C

6.1: TBAF / tetrahydrofuran / 3 h / 0 °C

7.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

8.1: DIBAL-H

9.1: (+)-DIPT

10.1: CCl₄; Ph₃P; NaHCO₃

11.1: LDA

12.1: Red-Al / diethyl ether / 2 h / 0 - 20 °C

13.1: Et₂Zn / CH₂Cl₂ / 4 h / -20 - 0 °C

14.1: Et₃N; DMAP / CH₂Cl₂ / 1 h / 0 - 20 °C

15.1: H₂ / Pd/C / hexane / 1 h / 20 °C

16.1: SO₃-pyridine; Et₃N / CH₂Cl₂ / 1 h / 0 - 20 °C

17.1: diethyl ether / 1 h / 0 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; tetrachloromethane; dmap; oxalyl dichloride; pyridine-SO₃ complex; L-(+)-diisopropyl tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; diethylzinc; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Sharpless epoxidation / 7.1: Swern oxidation / 10.1: Sharpless epoxidation;

DOI:10.1016/j.tetlet.2006.01.130

Reference yield:

(E)-4-((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-but-2-enoic acid ethyl ester → (2S,3S,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-6-[(S)-2-((1S,2S)-2-methyl-cyclopropyl)-2-triethylsilanyloxy-ethyl]-2-vinyl-tetrahydro-pyran (884338-32-3)

Guidance literature:

Multi-step reaction with 19 steps

1.1: DIBAL-H / CH₂Cl₂ / 0.33 h / -78 °C

2.1: D-(-)-DIPT; Ti(O-iPr)4; TBHP / CH₂Cl₂ / 3 h / -20 °C

2.2: 92 percent / Red-Al / tetrahydrofuran / 3 h / -10 °C

3.1: Et₃N; DMAP / dimethylformamide / 5 h / 0 - 20 °C

4.1: Et₃N; DMAP / CH₂Cl₂ / 0.5 h / 0 - 20 °C

5.1: CSA / methanol / 48 h / 20 °C

6.1: imidazole; DMAP / dimethylformamide / 24 h / 0 - 20 °C

7.1: TBAF / tetrahydrofuran / 3 h / 0 °C

8.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

9.1: DIBAL-H

10.1: (+)-DIPT

11.1: CCl₄; Ph₃P; NaHCO₃

12.1: LDA

13.1: Red-Al / diethyl ether / 2 h / 0 - 20 °C

14.1: Et₂Zn / CH₂Cl₂ / 4 h / -20 - 0 °C

15.1: Et₃N; DMAP / CH₂Cl₂ / 1 h / 0 - 20 °C

16.1: H₂ / Pd/C / hexane / 1 h / 20 °C

17.1: SO₃-pyridine; Et₃N / CH₂Cl₂ / 1 h / 0 - 20 °C

18.1: diethyl ether / 1 h / 0 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; tetrachloromethane; dmap; oxalyl dichloride; pyridine-SO₃ complex; L-(+)-diisopropyl tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; diethylzinc; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 2.1: Sharpless epoxidation / 8.1: Swern oxidation / 11.1: Sharpless epoxidation;

DOI:10.1016/j.tetlet.2006.01.130

Reference yield:

2-((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-ethanol → (2S,3S,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-6-[(S)-2-((1S,2S)-2-methyl-cyclopropyl)-2-triethylsilanyloxy-ethyl]-2-vinyl-tetrahydro-pyran (884338-32-3)

Guidance literature:

Multi-step reaction with 21 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

2.1: CH₂Cl₂ / 4 h / 20 °C

3.1: DIBAL-H / CH₂Cl₂ / 0.33 h / -78 °C

4.1: D-(-)-DIPT; Ti(O-iPr)4; TBHP / CH₂Cl₂ / 3 h / -20 °C

4.2: 92 percent / Red-Al / tetrahydrofuran / 3 h / -10 °C

5.1: Et₃N; DMAP / dimethylformamide / 5 h / 0 - 20 °C

6.1: Et₃N; DMAP / CH₂Cl₂ / 0.5 h / 0 - 20 °C

7.1: CSA / methanol / 48 h / 20 °C

8.1: imidazole; DMAP / dimethylformamide / 24 h / 0 - 20 °C

9.1: TBAF / tetrahydrofuran / 3 h / 0 °C

10.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

11.1: DIBAL-H

12.1: (+)-DIPT

13.1: CCl₄; Ph₃P; NaHCO₃

14.1: LDA

15.1: Red-Al / diethyl ether / 2 h / 0 - 20 °C

16.1: Et₂Zn / CH₂Cl₂ / 4 h / -20 - 0 °C

17.1: Et₃N; DMAP / CH₂Cl₂ / 1 h / 0 - 20 °C

18.1: H₂ / Pd/C / hexane / 1 h / 20 °C

19.1: SO₃-pyridine; Et₃N / CH₂Cl₂ / 1 h / 0 - 20 °C

20.1: diethyl ether / 1 h / 0 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; tetrachloromethane; dmap; oxalyl dichloride; pyridine-SO₃ complex; L-(+)-diisopropyl tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; diethylzinc; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Swern oxidation / 4.1: Sharpless epoxidation / 10.1: Swern oxidation / 13.1: Sharpless epoxidation;

DOI:10.1016/j.tetlet.2006.01.130

upstream raw materials:

Methylenetriphenylphosphorane

(E)-4-((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-but-2-en-1-ol

(S)-4-((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-butane-1,3-diol

(S)-1-[(2R,4S,5S,6R)-6-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-yl]-pent-3-yn-2-ol

Downstream raw materials:

C₆₉H₁₀₀O₉Si₃

{4-(tert-butyl-diphenyl-silanyloxy)-6-[2-({4-(tert-butyl-diphenyl-silanyloxy)-6-[2-hydroxy-2-(2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetoxy)-2-(2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid

(1S,5S,7R,9S,10S,11S,15S,17R,19S,20S)-9,19-Bis-(tert-butyl-diphenyl-silanyloxy)-10,20-dimethyl-5,15-bis-((1S,2S)-2-methyl-cyclopropyl)-4,14,21,22-tetraoxa-tricyclo[15.3.1.1^7,11]docosane-3,13-dione

{(2S,3S,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-6-[(S)-2-((1S,2S)-2-methyl-cyclopropyl)-2-triethylsilanyloxy-ethyl]-tetrahydro-pyran-2-yl}-acetic acid