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

Base Information

• Chemical Name: 3-[(2R,3aS,5R,6S,7aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-propionaldehyde
• CAS No.: 338799-39-6
• Molecular Formula: C₂₉H₄₀O₅Si
• Molecular Weight: 496.719
• Mol file: 338799-39-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about 3-[(2R,3aS,5R,6S,7aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-propionaldehyde 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: 68.0%

3-[(2R,3aS,5R,6S,7aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-propan-1-ol (338799-48-7) → 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)

Guidance literature:

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; In dichloromethane; at 20 ℃; for 0.416667h;

DOI:10.5555/ol015570y

Reference yield:

(+/-)-(E)-1-benzyloxy-2-methyl-4,7-octadiene (338799-35-2) → 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)

Guidance literature:

Multi-step reaction with 9 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

With 1H-imidazole; dmap; AD-mix-α; N-methyl-2-indolinone; tetrapropylammonium perruthennate; methanesulfonamide; N-triisopropylsulfonylimidazole; camphor-10-sulfonic acid; 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

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 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)

Guidance literature:

Multi-step reaction with 7 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

With 1H-imidazole; dmap; N-methyl-2-indolinone; tetrapropylammonium perruthennate; camphor-10-sulfonic acid; hydrogen; dimeric 9-borabicyclo[3.3.1]nonane; palladium dihydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate;

DOI:10.5555/ol015570y

upstream raw materials:

3-[(2R,3aS,5R,6S,7aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-propan-1-ol

tert-butylchlorodiphenylsilane

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

(+/-)-(E)-2-methyl-4,7-octadienoic acid

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

(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