1D-2,4,5,6-O-benzyl-3-deoxy-3-(benzyloxymethyl)-myo-inositol 2-[benzyl (R)-2-O-methyl-3-O-octadecyl phosphate]

Base Information

• Chemical Name: 1D-2,4,5,6-O-benzyl-3-deoxy-3-(benzyloxymethyl)-myo-inositol 2-[benzyl (R)-2-O-methyl-3-O-octadecyl phosphate]
• CAS No.: 290812-51-0
• Molecular Formula: C₇₁H₉₅O₁₁P
• Molecular Weight: 1155.5
• Mol file: 290812-51-0.mol

Synonyms:1D-2,4,5,6-O-benzyl-3-deoxy-3-(benzyloxymethyl)-myo-inositol 2-[benzyl (R)-2-O-methyl-3-O-octadecyl phosphate]

Chemical Property of 1D-2,4,5,6-O-benzyl-3-deoxy-3-(benzyloxymethyl)-myo-inositol 2-[benzyl (R)-2-O-methyl-3-O-octadecyl phosphate]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1D-2,4,5,6-O-benzyl-3-deoxy-3-(benzyloxymethyl)-myo-inositol 2-[benzyl (R)-2-O-methyl-3-O-octadecyl phosphate]

There total 13 articles about 1D-2,4,5,6-O-benzyl-3-deoxy-3-(benzyloxymethyl)-myo-inositol 2-[benzyl (R)-2-O-methyl-3-O-octadecyl 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:

Phosphorous acid benzyl ester (R)-2-methoxy-3-octadecyloxy-propyl ester (1R,2R,3S,4R,5R,6R)-2,3,4,6-tetrakis-benzyloxy-5-benzyloxymethyl-cyclohexyl ester → 1D-2,4,5,6-O-benzyl-3-deoxy-3-(benzyloxymethyl)-myo-inositol 2-[benzyl (R)-2-O-methyl-3-O-octadecyl phosphate] (290812-51-0)

Guidance literature:

With tert.-butylhydroperoxide; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1021/jm000117y

Reference yield:

1L-(1,2,4,6/3,5)-3,4,5-tri-O-benzyl-6-benzyloxymethyl-1,2,3,4,5-cyclohexanepentol (148983-67-9) → 1D-2,4,5,6-O-benzyl-3-deoxy-3-(benzyloxymethyl)-myo-inositol 2-[benzyl (R)-2-O-methyl-3-O-octadecyl phosphate] (290812-51-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: Bu₂SnO / toluene / 2 h / Heating

1.2: 77 percent / CsF / toluene / -50 - 20 °C

2.1: NaH / dimethylformamide / 0.5 h / 0 °C

2.2: 99 percent / n-Bu₄NI

3.1: RhCl(PPh₃)3; DABCO / ethanol / 5 h / Heating

3.2: 100 percent / aq. HCl / acetone / 4 h / Heating

4.1: diisopropylammonium tetrazolide / CH₂Cl₂ / 20 °C

5.1: 1H-tetrazole / CH₂Cl₂ / 20 °C

6.1: t-BuOOH / CH₂Cl₂ / 4 h / 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-tetrazole; tert.-butylhydroperoxide; RhCl(PPh₃)3; N,N-diisopropylamine tetrazolide; sodium hydride; di(n-butyl)tin oxide; In ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Stannylation / 1.2: Allylation / 2.1: Metallation / 2.2: Benzylation / 3.1: Isomerization / 3.2: Acidolysis / 4.1: Phosphorylation / 5.1: Condensation / 6.1: Oxidation;

DOI:10.1021/jm000117y

Reference yield:

(3aS,4aS,7aR,8S,8aS)-8-Benzyloxy-2,2,6,6-tetramethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-one → 1D-2,4,5,6-O-benzyl-3-deoxy-3-(benzyloxymethyl)-myo-inositol 2-[benzyl (R)-2-O-methyl-3-O-octadecyl phosphate] (290812-51-0)

Guidance literature:

Multi-step reaction with 12 steps

1.1: n-BuLi / tetrahydrofuran / 1 h / 0 °C

1.2: 54 percent / tetrahydrofuran / -78 - 20 °C

2.1: 9-BBN / tetrahydrofuran / 2 h / 50 °C

2.2: 42 percent / aq. NaOH; H₂O₂ / tetrahydrofuran; ethanol / 1 h / 50 °C

3.1: NaH / dimethylformamide / 0.5 h / 0 °C

4.1: AcCl / CH₂Cl₂; methanol / 0.33 h

5.1: NaH / dimethylformamide / 0.5 h / 0 °C

5.2: 5 h

6.1: HCl / methanol / 24 h / 20 °C

7.1: Bu₂SnO / toluene / 2 h / Heating

7.2: 77 percent / CsF / toluene / -50 - 20 °C

8.1: NaH / dimethylformamide / 0.5 h / 0 °C

8.2: 99 percent / n-Bu₄NI

9.1: RhCl(PPh₃)3; DABCO / ethanol / 5 h / Heating

9.2: 100 percent / aq. HCl / acetone / 4 h / Heating

10.1: diisopropylammonium tetrazolide / CH₂Cl₂ / 20 °C

11.1: 1H-tetrazole / CH₂Cl₂ / 20 °C

12.1: t-BuOOH / CH₂Cl₂ / 4 h / 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-tetrazole; hydrogenchloride; tert.-butylhydroperoxide; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; RhCl(PPh₃)3; N,N-diisopropylamine tetrazolide; sodium hydride; di(n-butyl)tin oxide; acetyl chloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Metallation / 1.2: Methylenation / 2.1: Hydroboration / 2.2: Oxidation / 3.1: Metallation / 3.2: Benzylation / 4.1: Acidolysis / 5.1: Metallation / 5.2: Benzylation / 6.1: Acidolysis / 7.1: Stannylation / 7.2: Allylation / 8.1: Metallation / 8.2: Benzylation / 9.1: Isomerization / 9.2: Acidolysis / 10.1: Phosphorylation / 11.1: Condensation / 12.1: Oxidation;

DOI:10.1021/jm000117y

upstream raw materials:

1L-(1,2,4,6/3,5)-3,4,5-tri-O-benzyl-6-benzyloxymethyl-1,2,3,4,5-cyclohexanepentol

(3aR,4R,4aR,7aR,8S,8aS)-8-Benzyloxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-ol

1D-6-O-benzyl-3-deoxy-1,2:4,5-di-O-isopropylidene-3-methylene-myo-inositol

1D-6-O-benzyl-3-deoxy-6-(hydroxymethyl)-1,2:4,5-di-O-isopropylidene-chiro-inositol