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

Base Information

• Chemical Name: {(2S,3S,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[(S)-2-hydroxy-2-((1S,2S)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid allyl ester
• CAS No.: 884338-34-5
• Molecular Formula: C₃₃H₄₆O₅Si
• Molecular Weight: 550.811
• Mol file: 884338-34-5.mol

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

Chemical Property of {(2S,3S,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[(S)-2-hydroxy-2-((1S,2S)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid allyl ester

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)-6-[(S)-2-hydroxy-2-((1S,2S)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid allyl ester

There total 24 articles about {(2S,3S,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[(S)-2-hydroxy-2-((1S,2S)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid allyl ester 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)-6-[(S)-2-hydroxy-2-((1S,2S)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid allyl ester (884338-34-5)

Guidance literature:

Multi-step reaction with 24 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

With 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; 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; 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;

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)-6-[(S)-2-hydroxy-2-((1S,2S)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid allyl ester (884338-34-5)

Guidance literature:

Multi-step reaction with 25 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

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

19.2: H₂O₂; NaOH / tetrahydrofuran; H₂O

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

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

22.1: diethyl ether / 0.17 h / 0 °C

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

24.1: K₂CO₃ / 1 h / 20 °C

With 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; 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; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 2.1: Sharpless epoxidation / 8.1: Swern oxidation / 11.1: Sharpless epoxidation;

DOI:10.1016/j.tetlet.2006.01.130

Reference yield:

(S)-4-((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-butane-1,3-diol (884338-26-5) → {(2S,3S,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[(S)-2-hydroxy-2-((1S,2S)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid allyl ester (884338-34-5)

Guidance literature:

Multi-step reaction with 23 steps

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

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

3.1: CSA / methanol / 48 h / 20 °C

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

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

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

7.1: DIBAL-H

8.1: (+)-DIPT

9.1: CCl₄; Ph₃P; NaHCO₃

10.1: LDA

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

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

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

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

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

16.1: diethyl ether / 1 h / 0 - 20 °C

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

17.2: H₂O₂; NaOH / tetrahydrofuran; H₂O

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

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

20.1: diethyl ether / 0.17 h / 0 °C

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

22.1: K₂CO₃ / 1 h / 20 °C

With 1H-imidazole; tetrachloromethane; dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; pyridine-SO₃ complex; L-(+)-diisopropyl tartrate; dimethylsulfide borane complex; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; diethylzinc; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; 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; tert-butyl alcohol; 6.1: Swern oxidation / 9.1: Sharpless epoxidation;

DOI:10.1016/j.tetlet.2006.01.130

upstream raw materials:

allyl alcohol

(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

Downstream raw materials:

(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

{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

C₆₉H₁₀₀O₉Si₃