{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

Base Information

• Chemical Name: {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
• CAS No.: 884338-36-7
• Molecular Formula: C₆₀H₈₂O₉Si₂
• Molecular Weight: 1003.48
• Mol file: 884338-36-7.mol

Synonyms:{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

Chemical Property of {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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {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

There total 29 articles about {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 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:

C63H86O9Si2 → {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 (884338-36-7)

Guidance literature:

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2006.01.130

Reference yield:

((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-acetaldehyde → {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 (884338-36-7)

Guidance literature:

Multi-step reaction with 29 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

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 → {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 (884338-36-7)

Guidance literature:

Multi-step reaction with 30 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

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

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