(1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-5-methyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

Base Information

• Chemical Name: (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-5-methyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane
• CAS No.: 219601-01-1
• Molecular Formula: C₃₃H₃₅N₃O₇
• Molecular Weight: 585.657

Synonyms:(1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-5-methyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

Chemical Property of (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-5-methyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-5-methyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

There total 28 articles about (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-5-methyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane 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: 92.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + (1R,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-5-methyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane (219601-00-0) → (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-5-methyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane (219601-01-1)

Guidance literature:

With pyridine;

DOI:10.1081/NCN-120022818

Reference yield:

1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-erythro-pentofuranosyl)thymine (293751-06-1) → (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-5-methyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane (219601-01-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 93 percent / pyridine

2: 91 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile

3: 98 percent / sulfuric acid / H₂O; acetone / Heating

4: 80 percent / 4-(dimethylamino)pyridine; pyridine / CH₂Cl₂ / 0 °C

5: 91 percent / sodium azide; 15-croen-5 / dimethylformamide

6: 93 percent / trimethylphosphine; NaOH / H₂O; tetrahydrofuran

7: 90 percent / HCO₂H

8: sodium methoxide / dimethylformamide

9: 97 percent / hydrogen; acetic acid / Pd(OH)2/C

10: 92 percent / pyridine

With pyridine; dmap; sodium hydroxide; formic acid; sodium azide; 15-crown-5; sulfuric acid; hydrogen; sodium methylate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trimethylphosphane; palladium dihydroxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 7: Eschweiler-Clarke reaction;

DOI:10.1081/NCN-120022818

Reference yield:

1-(3-O-benzyl-2,5-di-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl)thymine (293751-07-2) → (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-5-methyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane (219601-01-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 91 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile

2: 98 percent / sulfuric acid / H₂O; acetone / Heating

3: 80 percent / 4-(dimethylamino)pyridine; pyridine / CH₂Cl₂ / 0 °C

4: 91 percent / sodium azide; 15-croen-5 / dimethylformamide

5: 93 percent / trimethylphosphine; NaOH / H₂O; tetrahydrofuran

6: 90 percent / HCO₂H

7: sodium methoxide / dimethylformamide

8: 97 percent / hydrogen; acetic acid / Pd(OH)2/C

9: 92 percent / pyridine

With pyridine; dmap; sodium hydroxide; formic acid; sodium azide; 15-crown-5; sulfuric acid; hydrogen; sodium methylate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trimethylphosphane; palladium dihydroxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 6: Eschweiler-Clarke reaction;

DOI:10.1081/NCN-120022818

upstream raw materials:

4,4'-dimethoxytrityl chloride

(1R,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-5-methyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-erythro-pentofuranosyl)thymine

1-(3-O-benzyl-2,5-di-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl)thymine

Downstream raw materials:

(1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-5-N-methyl-3-(4-amino-5-methyl-cytosine-1-yl)-2-oxa-5-azabicyclo[2:2:1]heptane

Acetic acid (1R,3R,4R,7S)-1-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-methyl-3-(5-methyl-2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-2-oxa-5-aza-bicyclo[2.2.1]hept-7-yl ester

(1R,3R,4R,7S)-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-5-methyl-3-(4-benzoyl-5-methylcytosin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

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