3-(4-Methoxybenzyl)-1--2,6-dideoxy-3,4:9,10-di-O-isopropylidene-7-O-(methoxymethyl)-L-allo-β-D-galacto-undecodialdo-1,5-pyranoside-11,8-furanosyl>uracil

Base Information

• Chemical Name: 3-(4-Methoxybenzyl)-1--2,6-dideoxy-3,4:9,10-di-O-isopropylidene-7-O-(methoxymethyl)-L-allo-β-D-galacto-undecodialdo-1,5-pyranoside-11,8-furanosyl>uracil
• CAS No.: 121846-09-1
• Molecular Formula: C₄₀H₅₁N₃O₁₄
• Molecular Weight: 797.857
• Mol file: 121846-09-1.mol

Synonyms:3-(4-Methoxybenzyl)-1--2,6-dideoxy-3,4:9,10-di-O-isopropylidene-7-O-(methoxymethyl)-L-allo-β-D-galacto-undecodialdo-1,5-pyranoside-11,8-furanosyl>uracil

Chemical Property of 3-(4-Methoxybenzyl)-1--2,6-dideoxy-3,4:9,10-di-O-isopropylidene-7-O-(methoxymethyl)-L-allo-β-D-galacto-undecodialdo-1,5-pyranoside-11,8-furanosyl>uracil

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(4-Methoxybenzyl)-1--2,6-dideoxy-3,4:9,10-di-O-isopropylidene-7-O-(methoxymethyl)-L-allo-β-D-galacto-undecodialdo-1,5-pyranoside-11,8-furanosyl>uracil

There total 16 articles about 3-(4-Methoxybenzyl)-1--2,6-dideoxy-3,4:9,10-di-O-isopropylidene-7-O-(methoxymethyl)-L-allo-β-D-galacto-undecodialdo-1,5-pyranoside-11,8-furanosyl>uracil 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:

2',3'-O-isopropylideneuridine (362-43-6) → 3-(4-Methoxybenzyl)-1--2,6-dideoxy-3,4:9,10-di-O-isopropylidene-7-O-(methoxymethyl)-L-allo-β-D-galacto-undecodialdo-1,5-pyranoside-11,8-furanosyl>uracil (121846-09-1)

Guidance literature:

Multi-step reaction with 16 steps

1: 100 percent / triethylamine / CH₂Cl₂ / 0.08 h / Ambient temperature

2: NaH / dimethylformamide / 0.17 h / 0 °C

3: K₂CO₃ / methanol / 2 h / Ambient temperature

4: 79 percent / dimethyl sulfoxide, trifluoroacetic acid, pyridine, dicyclohexylcarbodiimide / benzene / 6 h / 5 °C

5: 67 percent / boron trifluoride etherate / various solvent(s) / 3 h / -78 °C

6: 96 percent / diisopropylethylamine / dimethylformamide / 3 h / Heating

7: osmium tetroxide, 4-methylmorpholine N-oxide, H₂O / tetrahydrofuran / 4 h / Ambient temperature

8: lead tetraacetate, sodium carbonate / CH₂Cl₂ / 0.08 h / 0 °C

9: 1.) tin tetrachloride; 2.) 5percent HF-CH₃CN / 1.) CH₂Cl₂, -78 deg C, 15 min; 2.) 0 deg C, 10 min

10: CeCl₃*7H₂O, NaBH₄ / ethanol; CH₂Cl₂ / 0.5 h / -78 °C

11: 91 percent / K₂CO₃ / methanol / 0.25 h / Ambient temperature

12: 87 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 0.5 h / 0 °C

13: 84 percent / cyclohexane; CH₂Cl₂ / 24 h / Irradiation

14: 83 percent / pyridinium p-toluenesulfonate / 0.08 h / 0 °C

15: H₂, Raney nickel / methanol; acetic acid / 4 h / 2068.6 - 2327.2 Torr

16: Na₂CO₃ / tetrahydrofuran; H₂O / 1 h / Ambient temperature

With pyridine; lead(IV) acetate; sodium tetrahydroborate; osmium(VIII) oxide; cerium(III) chloride; boron trifluoride diethyl etherate; hydrogen fluoride; water; hydrogen; pyridinium p-toluenesulfonate; tin(IV) chloride; nickel; sodium hydride; sodium carbonate; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; acetonitrile; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; cyclohexane; water; acetic acid; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja00197a047

Reference yield:

1-(5-O-Acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)uracil (15922-23-3) → 3-(4-Methoxybenzyl)-1--2,6-dideoxy-3,4:9,10-di-O-isopropylidene-7-O-(methoxymethyl)-L-allo-β-D-galacto-undecodialdo-1,5-pyranoside-11,8-furanosyl>uracil (121846-09-1)

Guidance literature:

Multi-step reaction with 15 steps

1: NaH / dimethylformamide / 0.17 h / 0 °C

2: K₂CO₃ / methanol / 2 h / Ambient temperature

3: 79 percent / dimethyl sulfoxide, trifluoroacetic acid, pyridine, dicyclohexylcarbodiimide / benzene / 6 h / 5 °C

4: 67 percent / boron trifluoride etherate / various solvent(s) / 3 h / -78 °C

5: 96 percent / diisopropylethylamine / dimethylformamide / 3 h / Heating

6: osmium tetroxide, 4-methylmorpholine N-oxide, H₂O / tetrahydrofuran / 4 h / Ambient temperature

7: lead tetraacetate, sodium carbonate / CH₂Cl₂ / 0.08 h / 0 °C

8: 1.) tin tetrachloride; 2.) 5percent HF-CH₃CN / 1.) CH₂Cl₂, -78 deg C, 15 min; 2.) 0 deg C, 10 min

9: CeCl₃*7H₂O, NaBH₄ / ethanol; CH₂Cl₂ / 0.5 h / -78 °C

10: 91 percent / K₂CO₃ / methanol / 0.25 h / Ambient temperature

11: 87 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 0.5 h / 0 °C

12: 84 percent / cyclohexane; CH₂Cl₂ / 24 h / Irradiation

13: 83 percent / pyridinium p-toluenesulfonate / 0.08 h / 0 °C

14: H₂, Raney nickel / methanol; acetic acid / 4 h / 2068.6 - 2327.2 Torr

15: Na₂CO₃ / tetrahydrofuran; H₂O / 1 h / Ambient temperature

With pyridine; lead(IV) acetate; sodium tetrahydroborate; osmium(VIII) oxide; cerium(III) chloride; boron trifluoride diethyl etherate; hydrogen fluoride; water; hydrogen; pyridinium p-toluenesulfonate; tin(IV) chloride; nickel; sodium hydride; sodium carbonate; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; acetonitrile; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; cyclohexane; water; acetic acid; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja00197a047

Reference yield:

(3aR,4S,6R,6aS)-6-(3-(4-methoxybenzyl)-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl)-tetrahydro-2,2-dimethylfuro[3,4-d][1,3]dioxole-4-carbaldehyde (121845-98-5) → 3-(4-Methoxybenzyl)-1--2,6-dideoxy-3,4:9,10-di-O-isopropylidene-7-O-(methoxymethyl)-L-allo-β-D-galacto-undecodialdo-1,5-pyranoside-11,8-furanosyl>uracil (121846-09-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 67 percent / boron trifluoride etherate / various solvent(s) / 3 h / -78 °C

2: 96 percent / diisopropylethylamine / dimethylformamide / 3 h / Heating

3: osmium tetroxide, 4-methylmorpholine N-oxide, H₂O / tetrahydrofuran / 4 h / Ambient temperature

4: lead tetraacetate, sodium carbonate / CH₂Cl₂ / 0.08 h / 0 °C

5: 1.) tin tetrachloride; 2.) 5percent HF-CH₃CN / 1.) CH₂Cl₂, -78 deg C, 15 min; 2.) 0 deg C, 10 min

6: CeCl₃*7H₂O, NaBH₄ / ethanol; CH₂Cl₂ / 0.5 h / -78 °C

7: 91 percent / K₂CO₃ / methanol / 0.25 h / Ambient temperature

8: 87 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 0.5 h / 0 °C

9: 84 percent / cyclohexane; CH₂Cl₂ / 24 h / Irradiation

10: 83 percent / pyridinium p-toluenesulfonate / 0.08 h / 0 °C

11: H₂, Raney nickel / methanol; acetic acid / 4 h / 2068.6 - 2327.2 Torr

12: Na₂CO₃ / tetrahydrofuran; H₂O / 1 h / Ambient temperature

With lead(IV) acetate; sodium tetrahydroborate; osmium(VIII) oxide; cerium(III) chloride; boron trifluoride diethyl etherate; hydrogen fluoride; water; hydrogen; pyridinium p-toluenesulfonate; tin(IV) chloride; nickel; sodium carbonate; potassium carbonate; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; acetonitrile; In tetrahydrofuran; methanol; ethanol; dichloromethane; cyclohexane; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/ja00197a047

upstream raw materials:

benzyl chloroformate

2',3'-O-isopropylideneuridine

1-(5-O-Acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)uracil

(3aR,4S,6R,6aS)-6-(3-(4-methoxybenzyl)-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl)-tetrahydro-2,2-dimethylfuro[3,4-d][1,3]dioxole-4-carbaldehyde

Downstream raw materials:

1-<(11R)-1,3,4,7,9,10-Hexa-O-acetyl-2-<(benzyloxycarbonyl)amino>-2,6-dideoxy-L-allo-α-D-galacto-undecodialdo-1,5-pyranose-11,8-furanosyl>-3-(4-methoxybenzyl)uracil

1-<(11R)-1,3,4,7,9,10-Hexa-O-acetyl-2-<(benzyloxycarbonyl)amino>-2,6-dideoxy-L-allo-β-D-galacto-undecodialdo-1,5-pyranose-11,8-furanosyl>-3-(4-methoxybenzyl)uracil