(Z)-(S)-1-[(2R,3aS,5R,6S,7aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-8-(4-methoxy-benzyloxy)-7-triethylsilanyloxy-oct-4-en-3-one

Base Information

• Chemical Name: (Z)-(S)-1-[(2R,3aS,5R,6S,7aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-8-(4-methoxy-benzyloxy)-7-triethylsilanyloxy-oct-4-en-3-one
• CAS No.: 338799-30-7
• Molecular Formula: C₄₈H₇₀O₈Si₂
• Molecular Weight: 831.25
• Mol file: 338799-30-7.mol

Synonyms:(Z)-(S)-1-[(2R,3aS,5R,6S,7aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-8-(4-methoxy-benzyloxy)-7-triethylsilanyloxy-oct-4-en-3-one

Chemical Property of (Z)-(S)-1-[(2R,3aS,5R,6S,7aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-8-(4-methoxy-benzyloxy)-7-triethylsilanyloxy-oct-4-en-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(S)-1-[(2R,3aS,5R,6S,7aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-8-(4-methoxy-benzyloxy)-7-triethylsilanyloxy-oct-4-en-3-one

There total 23 articles about (Z)-(S)-1-[(2R,3aS,5R,6S,7aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-8-(4-methoxy-benzyloxy)-7-triethylsilanyloxy-oct-4-en-3-one 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:

tert-butylchlorodiphenylsilane (58479-61-1) → (Z)-(S)-1-[(2R,3aS,5R,6S,7aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-8-(4-methoxy-benzyloxy)-7-triethylsilanyloxy-oct-4-en-3-one (338799-30-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 80 percent / imidazole; 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 8 h

2.1: 95 percent / H₂ / Pd(OH)2/C / ethyl acetate

3.1: TPAP; NMO / CH₂Cl₂

4.1: diethyl ether / 0.5 h / -78 °C

5.1: 80 mg / CSA / CH₂Cl₂ / 2 h / 0 - 20 °C

6.1: 9-BBN dimer / tetrahydrofuran / 2 h / 0 - 20 °C

6.2: 81 percent / H₂O₂; NaOH / tetrahydrofuran / 0 - 20 °C

7.1: 68 percent / TPAP; NMO / CH₂Cl₂ / 0.42 h / 20 °C

8.1: EtMgBr / tetrahydrofuran; diethyl ether / 0 - 20 °C

8.2: 72 percent / tetrahydrofuran; diethyl ether / -60 - -40 °C

9.1: H₂ / Pd/CaCO₃ with Pb / benzene / 1 h

10.1: 22 mg / TPAP; NMO / CH₂Cl₂ / 0.67 h / 20 °C

With 1H-imidazole; dmap; N-methyl-2-indolinone; tetrapropylammonium perruthennate; camphor-10-sulfonic acid; ethylmagnesium bromide; hydrogen; dimeric 9-borabicyclo[3.3.1]nonane; palladium dihydroxide; Lindlar's catalyst; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; benzene; 9.1: Lindlar reduction;

DOI:10.5555/ol015570y

Reference yield:

(+/-)-(E)-1-benzyloxy-2-methyl-4,7-octadiene (338799-35-2) → (Z)-(S)-1-[(2R,3aS,5R,6S,7aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-8-(4-methoxy-benzyloxy)-7-triethylsilanyloxy-oct-4-en-3-one (338799-30-7)

Guidance literature:

Multi-step reaction with 12 steps

1.1: AD-mix α; CH3SO2NH2 / H2O; 2-methyl-propan-2-ol / 13 h / 0 °C

2.1: KHMDS; N-triisopropylsulfonylimidazole / tetrahydrofuran / 0 - 20 °C

2.2: 50 percent / KHMDS / tetrahydrofuran / 0 - 20 °C

3.1: 80 percent / imidazole; 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 8 h

4.1: 95 percent / H₂ / Pd(OH)2/C / ethyl acetate

5.1: TPAP; NMO / CH₂Cl₂

6.1: diethyl ether / 0.5 h / -78 °C

7.1: 80 mg / CSA / CH₂Cl₂ / 2 h / 0 - 20 °C

8.1: 9-BBN dimer / tetrahydrofuran / 2 h / 0 - 20 °C

8.2: 81 percent / H₂O₂; NaOH / tetrahydrofuran / 0 - 20 °C

9.1: 68 percent / TPAP; NMO / CH₂Cl₂ / 0.42 h / 20 °C

10.1: EtMgBr / tetrahydrofuran; diethyl ether / 0 - 20 °C

10.2: 72 percent / tetrahydrofuran; diethyl ether / -60 - -40 °C

11.1: H₂ / Pd/CaCO₃ with Pb / benzene / 1 h

12.1: 22 mg / TPAP; NMO / CH₂Cl₂ / 0.67 h / 20 °C

With 1H-imidazole; dmap; AD-mix-α; N-methyl-2-indolinone; tetrapropylammonium perruthennate; methanesulfonamide; N-triisopropylsulfonylimidazole; camphor-10-sulfonic acid; ethylmagnesium bromide; hydrogen; potassium hexamethylsilazane; dimeric 9-borabicyclo[3.3.1]nonane; palladium dihydroxide; Lindlar's catalyst; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; tert-butyl alcohol; benzene; 1.1: Sharpless asymmetric dihydroxylation / 11.1: Lindlar reduction;

DOI:10.5555/ol015570y

Reference yield:

(+/-)-(E)-2-methyl-4,7-octadien-1-ol (338799-45-4) → (Z)-(S)-1-[(2R,3aS,5R,6S,7aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-8-(4-methoxy-benzyloxy)-7-triethylsilanyloxy-oct-4-en-3-one (338799-30-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: NaH / tetrahydrofuran; various solvent(s) / 1 h / 0 - 20 °C

1.2: 90 percent / TBAI / tetrahydrofuran; various solvent(s) / 15 h / 20 °C

2.1: AD-mix α; CH3SO2NH2 / H2O; 2-methyl-propan-2-ol / 13 h / 0 °C

3.1: KHMDS; N-triisopropylsulfonylimidazole / tetrahydrofuran / 0 - 20 °C

3.2: 50 percent / KHMDS / tetrahydrofuran / 0 - 20 °C

4.1: 80 percent / imidazole; 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 8 h

5.1: 95 percent / H₂ / Pd(OH)2/C / ethyl acetate

6.1: TPAP; NMO / CH₂Cl₂

7.1: diethyl ether / 0.5 h / -78 °C

8.1: 80 mg / CSA / CH₂Cl₂ / 2 h / 0 - 20 °C

9.1: 9-BBN dimer / tetrahydrofuran / 2 h / 0 - 20 °C

9.2: 81 percent / H₂O₂; NaOH / tetrahydrofuran / 0 - 20 °C

10.1: 68 percent / TPAP; NMO / CH₂Cl₂ / 0.42 h / 20 °C

11.1: EtMgBr / tetrahydrofuran; diethyl ether / 0 - 20 °C

11.2: 72 percent / tetrahydrofuran; diethyl ether / -60 - -40 °C

12.1: H₂ / Pd/CaCO₃ with Pb / benzene / 1 h

13.1: 22 mg / TPAP; NMO / CH₂Cl₂ / 0.67 h / 20 °C

With 1H-imidazole; dmap; AD-mix-α; N-methyl-2-indolinone; tetrapropylammonium perruthennate; methanesulfonamide; N-triisopropylsulfonylimidazole; camphor-10-sulfonic acid; ethylmagnesium bromide; hydrogen; potassium hexamethylsilazane; sodium hydride; dimeric 9-borabicyclo[3.3.1]nonane; palladium dihydroxide; Lindlar's catalyst; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; tert-butyl alcohol; benzene; 2.1: Sharpless asymmetric dihydroxylation / 12.1: Lindlar reduction;

DOI:10.5555/ol015570y

upstream raw materials:

triethylsilyl chloride

p-methoxybenzyl chloride

tert-butylchlorodiphenylsilane

(+/-)-(E)-2-methyl-4,7-octadien-1-ol