C₃₉H₆₁O₉PSi

Base Information

• Chemical Name: C₃₉H₆₁O₉PSi
• CAS No.: 1443743-45-0
• Molecular Formula: C₃₉H₆₁O₉PSi
• Molecular Weight: 732.967
• Mol file: 1443743-45-0.mol

Synonyms:C₃₉H₆₁O₉PSi

Chemical Property of C₃₉H₆₁O₉PSi

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₃₉H₆₁O₉PSi

There total 20 articles about C₃₉H₆₁O₉PSi 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: 81.0%

C39H63O9PSi (1443743-60-9) → C39H61O9PSi (1443743-45-0)

Guidance literature:

With sulfur trioxide pyridine complex; triethylamine; In dichloromethane; dimethyl sulfoxide; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol401367h

Reference yield:

(3S,4R)-dihydroxy-(2R)-(hydroxymethyl)tetrahydropyran (3971-47-9,7103-29-9,13035-11-5,26242-03-5) → C39H61O9PSi (1443743-45-0)

Guidance literature:

Multi-step reaction with 12 steps

1.1: camphor-10-sulfonic acid / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere

2.2: -15 - 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / toluene / 0.01 h / -78 - -10 °C / Inert atmosphere

4.1: triphenylphosphine; 1H-imidazole; iodine / tetrahydrofuran / 12 h / 55 °C / Inert atmosphere; Darkness

5.1: tert.-butyl lithium / tetrahydrofuran / 0.5 h / -78 - -60 °C / Inert atmosphere

5.2: -78 - 0 °C / Inert atmosphere

6.1: ozone; pyridine / dichloromethane / -78 °C / Inert atmosphere

6.2: -78 - 20 °C / Inert atmosphere

7.1: lithium chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 0.25 h / 20 °C / Inert atmosphere

7.2: 20 °C / Inert atmosphere

8.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 1 h / 20 °C / Inert atmosphere

9.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

9.2: 0.1 h / 0 °C / Inert atmosphere

10.1: n-butyllithium / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

10.2: 0.1 h / -78 °C / Inert atmosphere

11.1: camphor-10-sulfonic acid / dichloromethane; methanol / 0.1 h / 0 °C

12.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 1 h / 0 °C / Inert atmosphere

With pyridine; 1H-imidazole; n-butyllithium; palladium 10% on activated carbon; camphor-10-sulfonic acid; hydrogen; iodine; tert.-butyl lithium; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; sodium hydride; diisobutylaluminium hydride; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; 7.1: |Horner-Wadsworth-Emmons Olefination / 7.2: |Horner-Wadsworth-Emmons Olefination / 9.1: |Wittig Olefination / 9.2: |Wittig Olefination;

DOI:10.1021/ol401367h

Reference yield:

1,5-anhydro-2-deoxy-4,6-O-p-methoxybenzylidene-D-arabino-hexitol (203862-58-2) → C39H61O9PSi (1443743-45-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere

1.2: -15 - 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / toluene / 0.01 h / -78 - -10 °C / Inert atmosphere

3.1: triphenylphosphine; 1H-imidazole; iodine / tetrahydrofuran / 12 h / 55 °C / Inert atmosphere; Darkness

4.1: tert.-butyl lithium / tetrahydrofuran / 0.5 h / -78 - -60 °C / Inert atmosphere

4.2: -78 - 0 °C / Inert atmosphere

5.1: ozone; pyridine / dichloromethane / -78 °C / Inert atmosphere

5.2: -78 - 20 °C / Inert atmosphere

6.1: lithium chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 0.25 h / 20 °C / Inert atmosphere

6.2: 20 °C / Inert atmosphere

7.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 1 h / 20 °C / Inert atmosphere

8.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

8.2: 0.1 h / 0 °C / Inert atmosphere

9.1: n-butyllithium / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

9.2: 0.1 h / -78 °C / Inert atmosphere

10.1: camphor-10-sulfonic acid / dichloromethane; methanol / 0.1 h / 0 °C

11.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 1 h / 0 °C / Inert atmosphere

With pyridine; 1H-imidazole; n-butyllithium; palladium 10% on activated carbon; camphor-10-sulfonic acid; hydrogen; iodine; tert.-butyl lithium; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; sodium hydride; diisobutylaluminium hydride; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; 6.1: |Horner-Wadsworth-Emmons Olefination / 6.2: |Horner-Wadsworth-Emmons Olefination / 8.1: |Wittig Olefination / 8.2: |Wittig Olefination;

DOI:10.1021/ol401367h

upstream raw materials:

(3S,4R)-dihydroxy-(2R)-(hydroxymethyl)tetrahydropyran

1,5-anhydro-2-deoxy-4,6-O-p-methoxybenzylidene-D-arabino-hexitol

C₂₁H₂₄O₅

C₂₁H₂₅IO₄

Downstream raw materials:

C₂₉H₄₄O₄Si