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

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-octadecylcarbonate]
• CAS No.: 290812-53-2
• Molecular Formula: C₆₅H₈₈O₁₀
• Molecular Weight: 1029.41
• Mol file: 290812-53-2.mol

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

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

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-octadecylcarbonate]

There total 12 articles about 1D-2,4,5,6-O-benzyl-3-deoxy-3-(benzyloxymethyl)-myo-inositol 2-[benzyl (R)-2-O-methyl-3-O-octadecylcarbonate] 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:

(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-octadecylcarbonate] (290812-53-2)

Guidance literature:

Multi-step reaction with 11 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: toluene / 0.67 h / Heating

11.1: DBU / toluene / 4 h / Heating

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; RhCl(PPh₃)3; sodium hydride; di(n-butyl)tin oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 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: Carbonylation / 11.1: Esterification;

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-octadecylcarbonate] (290812-53-2)

Guidance literature:

Multi-step reaction with 5 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: toluene / 0.67 h / Heating

5.1: DBU / toluene / 4 h / Heating

With 1,4-diaza-bicyclo[2.2.2]octane; RhCl(PPh₃)3; sodium hydride; di(n-butyl)tin oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; 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: Carbonylation / 5.1: Esterification;

DOI:10.1021/jm000117y

Reference yield:

(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 (192122-41-1) → 1D-2,4,5,6-O-benzyl-3-deoxy-3-(benzyloxymethyl)-myo-inositol 2-[benzyl (R)-2-O-methyl-3-O-octadecylcarbonate] (290812-53-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: (COCl)2; DMSO / CH₂Cl₂ / 2 h / -78 °C

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

2.2: 54 percent / tetrahydrofuran / -78 - 20 °C

3.1: 9-BBN / tetrahydrofuran / 2 h / 50 °C

3.2: 42 percent / aq. NaOH; H₂O₂ / tetrahydrofuran; ethanol / 1 h / 50 °C

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

5.1: AcCl / CH₂Cl₂; methanol / 0.33 h

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

6.2: 5 h

7.1: HCl / methanol / 24 h / 20 °C

8.1: Bu₂SnO / toluene / 2 h / Heating

8.2: 77 percent / CsF / toluene / -50 - 20 °C

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

9.2: 99 percent / n-Bu₄NI

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

10.2: 100 percent / aq. HCl / acetone / 4 h / Heating

11.1: toluene / 0.67 h / Heating

12.1: DBU / toluene / 4 h / Heating

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; RhCl(PPh₃)3; sodium hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; acetyl chloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Oxidation / 2.1: Metallation / 2.2: Methylenation / 3.1: Hydroboration / 3.2: Oxidation / 4.1: Metallation / 4.2: Benzylation / 5.1: Acidolysis / 6.1: Metallation / 6.2: Benzylation / 7.1: Acidolysis / 8.1: Stannylation / 8.2: Allylation / 9.1: Metallation / 9.2: Benzylation / 10.1: Isomerization / 10.2: Acidolysis / 11.1: Carbonylation / 12.1: Esterification;

DOI:10.1021/jm000117y

upstream raw materials:

1-O-octadecyl-2-O-methyl-sn-glycerol

Imidazole-1-carboxylic acid (1R,2R,3S,4R,5R,6R)-2,3,4,6-tetrakis-benzyloxy-5-benzyloxymethyl-cyclohexyl ester

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

Refernces