(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-yn-3-ol

Base Information

• Chemical Name: (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-yn-3-ol
• CAS No.: 338799-41-0
• Molecular Formula: C₄₈H₇₀O₈Si₂
• Molecular Weight: 831.25
• Mol file: 338799-41-0.mol

Synonyms:(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-yn-3-ol

Chemical Property of (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-yn-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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-yn-3-ol

There total 20 articles about (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-yn-3-ol 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: 72.0%

Triethyl-[(S)-1-(4-methoxy-benzyloxymethyl)-but-3-ynyloxy]-silane (338799-40-9) + 3-[(2R,3aS,5R,6S,7aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-propionaldehyde (338799-39-6) → (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-yn-3-ol (338799-41-0)

Guidance literature:

Triethyl-[(S)-1-(4-methoxy-benzyloxymethyl)-but-3-ynyloxy]-silane; With ethylmagnesium bromide; In tetrahydrofuran; diethyl ether; at 0 - 20 ℃;

3-[(2R,3aS,5R,6S,7aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-propionaldehyde; In tetrahydrofuran; diethyl ether; at -60 - -40 ℃; Further stages.;

DOI:10.5555/ol015570y

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (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-yn-3-ol (338799-41-0)

Guidance literature:

Multi-step reaction with 8 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

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; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate;

DOI:10.5555/ol015570y

Reference yield:

(+/-)-(E)-1-benzyloxy-2-methyl-4,7-octadiene (338799-35-2) → (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-yn-3-ol (338799-41-0)

Guidance literature:

Multi-step reaction with 10 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

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; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; tert-butyl alcohol; 1.1: Sharpless asymmetric dihydroxylation;

DOI:10.5555/ol015570y

upstream raw materials:

Triethyl-[(S)-1-(4-methoxy-benzyloxymethyl)-but-3-ynyloxy]-silane

3-[(2R,3aS,5R,6S,7aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-propionaldehyde

triethylsilyl chloride

p-methoxybenzyl chloride

Downstream raw materials:

(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