2-O-benzyl-1-O-tert-butyldimethylsilyl-D-myo-inositol-3,4,5-tris(dibenzyl phosphate)

Base Information

• Chemical Name: 2-O-benzyl-1-O-tert-butyldimethylsilyl-D-myo-inositol-3,4,5-tris(dibenzyl phosphate)
• CAS No.: 910864-33-4
• Molecular Formula: C₆₁H₇₁O₁₅P₃Si
• Molecular Weight: 1165.23
• Mol file: 910864-33-4.mol

Synonyms:2-O-benzyl-1-O-tert-butyldimethylsilyl-D-myo-inositol-3,4,5-tris(dibenzyl phosphate)

Chemical Property of 2-O-benzyl-1-O-tert-butyldimethylsilyl-D-myo-inositol-3,4,5-tris(dibenzyl phosphate)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-benzyl-1-O-tert-butyldimethylsilyl-D-myo-inositol-3,4,5-tris(dibenzyl phosphate)

There total 11 articles about 2-O-benzyl-1-O-tert-butyldimethylsilyl-D-myo-inositol-3,4,5-tris(dibenzyl phosphate) 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: 70.0%

2-O-benzyl-1-O-tert-butyldimethylsilyl-D-myo-inositol-3,5-bis(dibenzyl phosphate) (910864-32-3) + Dibenzyl N,N-diisopropylphosphoramidite (108549-23-1) → 2-O-benzyl-1-O-tert-butyldimethylsilyl-D-myo-inositol-3,4,5-tris(dibenzyl phosphate) (910864-33-4)

Guidance literature:

2-O-benzyl-1-O-tert-butyldimethylsilyl-D-myo-inositol-3,5-bis(dibenzyl phosphate); Dibenzyl N,N-diisopropylphosphoramidite; With 4,5-dicyano-1H-imidazole; In dichloromethane; at 20 ℃; for 15h;

With dihydrogen peroxide; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/jo0610816

Reference yield:

2-O-benzyl-4,6-di-O-p-methoxybenzyl-D-myo-inositol-1,3,5-O-orthoformate → 2-O-benzyl-1-O-tert-butyldimethylsilyl-D-myo-inositol-3,4,5-tris(dibenzyl phosphate) (910864-33-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 55 percent / aq. HCl / methanol / 18 h / 20 °C

2.1: 53 percent / Et₃N / BocHis(Me)-[4S-tBuOPro]-[(CH₂)4-1,4-diylGly]-Tyr(tBu)-PheOMe / toluene

3.1: 90 percent / imidazole / dimethylformamide / 48 h / 50 °C

4.1: 88 percent / NaH / tetrahydrofuran / 1 h / 20 °C

5.1: 49 percent / AcCl / methanol / 12 h / 0 °C

6.1: 4,5-dicyanoimidazole / CH₂Cl₂ / 15 h / 20 °C

6.2: 87 percent / aq. H₂O₂ / CH₂Cl₂ / 1 h / 0 °C

7.1: 67 percent / DDQ / CH₂Cl₂; H₂O / 12 h / 20 °C

8.1: 4,5-dicyanoimidazole / CH₂Cl₂ / 15 h / 20 °C

8.2: 70 percent / aq. H₂O₂ / CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; hydrogenchloride; 4,5-dicyano-1H-imidazole; sodium hydride; triethylamine; acetyl chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; BocHis(Me)-[4S-tBuOPro]-[(CH₂)4-1,4-diylGly]-Tyr(tBu)-PheOMe; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo0610816

Reference yield:

2-O-benzyl-4,6-di-O-p-methoxybenzyl-D-myo-inositol (910864-22-1) → 2-O-benzyl-1-O-tert-butyldimethylsilyl-D-myo-inositol-3,4,5-tris(dibenzyl phosphate) (910864-33-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 53 percent / Et₃N / BocHis(Me)-[4S-tBuOPro]-[(CH₂)4-1,4-diylGly]-Tyr(tBu)-PheOMe / toluene

2.1: 90 percent / imidazole / dimethylformamide / 48 h / 50 °C

3.1: 88 percent / NaH / tetrahydrofuran / 1 h / 20 °C

4.1: 49 percent / AcCl / methanol / 12 h / 0 °C

5.1: 4,5-dicyanoimidazole / CH₂Cl₂ / 15 h / 20 °C

5.2: 87 percent / aq. H₂O₂ / CH₂Cl₂ / 1 h / 0 °C

6.1: 67 percent / DDQ / CH₂Cl₂; H₂O / 12 h / 20 °C

7.1: 4,5-dicyanoimidazole / CH₂Cl₂ / 15 h / 20 °C

7.2: 70 percent / aq. H₂O₂ / CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; 4,5-dicyano-1H-imidazole; sodium hydride; triethylamine; acetyl chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; BocHis(Me)-[4S-tBuOPro]-[(CH₂)4-1,4-diylGly]-Tyr(tBu)-PheOMe; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo0610816

upstream raw materials:

2-O-benzyl-1-O-tert-butyldimethylsilyl-D-myo-inositol-3,5-bis(dibenzyl phosphate)

Dibenzyl N,N-diisopropylphosphoramidite

2-O-benzyl-4,6-di-O-p-methoxybenzyl-D-myo-inositol

2-O-benzyl-4,6-di-O-p-methoxybenzyl-D-myo-inositol-3-diphenyl phosphate