(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

Base Information

• Chemical Name: (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
• CAS No.: 884338-37-8
• Molecular Formula: C₆₀H₈₀O₈Si₂
• Molecular Weight: 985.461
• Mol file: 884338-37-8.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 29 articles about (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 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:

((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-acetaldehyde → (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[15.3.1.17,11]docosane-3,13-dione (884338-37-8)

Guidance literature:

Multi-step reaction with 30 steps

1.1: CH₂Cl₂ / 4 h / 20 °C

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

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

3.2: 92 percent / Red-Al / tetrahydrofuran / 3 h / -10 °C

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

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

6.1: CSA / methanol / 48 h / 20 °C

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

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

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

10.1: DIBAL-H

11.1: (+)-DIPT

12.1: CCl₄; Ph₃P; NaHCO₃

13.1: LDA

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

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

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

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

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

19.1: diethyl ether / 1 h / 0 - 20 °C

20.1: BH₃*Me₂S / tetrahydrofuran / 0.5 h / 0 °C

20.2: H₂O₂; NaOH / tetrahydrofuran; H₂O

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

22.1: NaClO₂; NaH₂PO₄*2H₂O; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1 h / 20 °C

23.1: diethyl ether / 0.17 h / 0 °C

24.1: CSA / methanol; CH₂Cl₂ / 0.17 h / 0 °C

25.1: K₂CO₃ / 1 h / 20 °C

26.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 3 h / 20 °C

26.2: 80 percent / DMAP / toluene / 1 h / 20 °C

27.1: CSA / methanol; CH₂Cl₂ / 0.17 h / 0 °C

28.1: morpholine / Pd(PPh₃)4 / tetrahydrofuran / 1 h / 20 °C

29.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 3 h / 20 °C

29.2: 65 percent / DMAP / toluene / 5 h / 80 °C

With morpholine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; tetrachloromethane; dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; pyridine-SO₃ complex; L-(+)-diisopropyl tartrate; dimethylsulfide borane complex; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; diethylzinc; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium diisopropyl amide; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 3.1: Sharpless epoxidation / 9.1: Swern oxidation / 12.1: Sharpless epoxidation / 27.1: Yamaguchi reaction;

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 → (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[15.3.1.17,11]docosane-3,13-dione (884338-37-8)

Guidance literature:

Multi-step reaction with 31 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

21.1: BH₃*Me₂S / tetrahydrofuran / 0.5 h / 0 °C

21.2: H₂O₂; NaOH / tetrahydrofuran; H₂O

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

23.1: NaClO₂; NaH₂PO₄*2H₂O; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1 h / 20 °C

24.1: diethyl ether / 0.17 h / 0 °C

25.1: CSA / methanol; CH₂Cl₂ / 0.17 h / 0 °C

26.1: K₂CO₃ / 1 h / 20 °C

27.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 3 h / 20 °C

27.2: 80 percent / DMAP / toluene / 1 h / 20 °C

28.1: CSA / methanol; CH₂Cl₂ / 0.17 h / 0 °C

29.1: morpholine / Pd(PPh₃)4 / tetrahydrofuran / 1 h / 20 °C

30.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 3 h / 20 °C

30.2: 65 percent / DMAP / toluene / 5 h / 80 °C

With morpholine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; tetrachloromethane; dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; pyridine-SO₃ complex; L-(+)-diisopropyl tartrate; dimethylsulfide borane complex; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; diethylzinc; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium diisopropyl amide; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Swern oxidation / 4.1: Sharpless epoxidation / 10.1: Swern oxidation / 13.1: Sharpless epoxidation / 28.1: Yamaguchi reaction;

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-en-1-ol (884338-24-3) → (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[15.3.1.17,11]docosane-3,13-dione (884338-37-8)

Guidance literature:

Multi-step reaction with 28 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

18.1: BH₃*Me₂S / tetrahydrofuran / 0.5 h / 0 °C

18.2: H₂O₂; NaOH / tetrahydrofuran; H₂O

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

20.1: NaClO₂; NaH₂PO₄*2H₂O; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1 h / 20 °C

21.1: diethyl ether / 0.17 h / 0 °C

22.1: CSA / methanol; CH₂Cl₂ / 0.17 h / 0 °C

23.1: K₂CO₃ / 1 h / 20 °C

24.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 3 h / 20 °C

24.2: 80 percent / DMAP / toluene / 1 h / 20 °C

25.1: CSA / methanol; CH₂Cl₂ / 0.17 h / 0 °C

26.1: morpholine / Pd(PPh₃)4 / tetrahydrofuran / 1 h / 20 °C

27.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 3 h / 20 °C

27.2: 65 percent / DMAP / toluene / 5 h / 80 °C

With morpholine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; tetrachloromethane; dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; pyridine-SO₃ complex; L-(+)-diisopropyl tartrate; dimethylsulfide borane complex; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; diethylzinc; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium diisopropyl amide; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Sharpless epoxidation / 7.1: Swern oxidation / 10.1: Sharpless epoxidation / 25.1: Yamaguchi reaction;

DOI:10.1016/j.tetlet.2006.01.130

upstream raw materials:

(2R,3R,4S,6R)-2-Benzyloxymethyl-6-(2-hydroxy-ethyl)-3-methyl-tetrahydro-pyran-4-ol

(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

2-[(2R,4S,5S,6R)-6-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-yl]-ethanol