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

Base Information

• Chemical Name: (1R,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane
• CAS No.: 552856-44-7
• Molecular Formula: C₁₈H₂₁N₃O₅
• Molecular Weight: 359.382
• Mol file: 552856-44-7.mol

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

Chemical Property of (1R,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-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)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

There total 26 articles about (1R,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-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: 99.0%

(1R,3R,4R,7S)-1-benzoyloxymethyl-7-benzyloxy-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane (552856-43-6) → (1R,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane (552856-44-7)

Guidance literature:

With ammonia; In methanol; at 20 ℃; for 30h;

DOI:10.1039/b208864a

Reference yield:

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → (1R,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane (552856-44-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: pyridine / CH₂Cl₂ / 0 - 20 °C

2.1: aq. H₂SO₄ / acetic acid / 18 h / 20 °C

3.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 1 h / 0 °C

3.2: trimethylsilyl triflate / acetonitrile / 2 h / 65 °C

4.1: 84 percent / methanolic ammonia / methanol / 0 - 20 °C

5.1: pyridine / CH₂Cl₂ / 0 - 20 °C

6.1: 98 percent / DBU / dimethylformamide / 20 °C

7.1: 80 percent / aq. HCl / CH₂Cl₂ / 5 h / 80 °C

8.1: pyridine; trifluoroacetic anhydride / CH₂Cl₂ / 73 h / 0 - 7 °C

8.2: 25 percent / NaN₃ / dimethylformamide / 18.5 h / 20 - 80 °C

9.1: aq LiOH / tetrahydrofuran / 9 h

10.1: 2.91 g / pyridine / 0 - 20 °C

11.1: 93 percent / aq. NaOH; PMe₃ / tetrahydrofuran / 8 h / 20 °C

12.1: 97 percent / dimethylformamide / 5.5 h / 80 °C

13.1: 99 percent / NH₃ / methanol / 30 h / 20 °C

With pyridine; hydrogenchloride; lithium hydroxide; sodium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; ammonia; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic anhydride; trimethylphosphane; In tetrahydrofuran; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/b208864a

Reference yield:

1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-erythro-pentofuranosyl)thymine (293751-06-1) → (1R,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane (552856-44-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 96 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

2: 91 percent / DBU / acetonitrile / 2 h

3: 98 percent / aq. H₂SO₄ / acetone / Heating

4: 80 percent / pyridine; DMAP / CH₂Cl₂ / 1.5 h / 0 °C

5: 91 percent / NaN₃; 15-crown-5 / dimethylformamide / 1 h / 80 °C

6: 93 percent / aq. NaOH; PMe₃ / tetrahydrofuran / 8 h / 20 °C

7: 97 percent / dimethylformamide / 5.5 h / 80 °C

8: 99 percent / NH₃ / methanol / 30 h / 20 °C

With pyridine; dmap; sodium hydroxide; sodium azide; 15-crown-5; sulfuric acid; ammonia; 1,8-diazabicyclo[5.4.0]undec-7-ene; trimethylphosphane; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1039/b208864a

upstream raw materials:

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

5-O-benzoyl-4-C-benzoyloxymethyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

1,2-di-O-acetyl-5-O-benzoyl-4-C-benzoyloxymethyl-3-O-benzyl-D-erythro-pentofuranose

2,2-anhydro-1-(5-O-benzoyl-4-C-benzoyloxymethyl-3-O-benzyl-β-D-threo-pentofuranosyl)thymine

Downstream raw materials:

(1R,3R,4R,7S)-7-benzyloxy-1-(4,4'-dimethoxytrityl)oxymethyl-3-(thymin-1-yl)-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane

(1R,3R,4R,7S)-7-benzyloxy-1-(4,4'-dimethoxytrityl)oxymethyl-3-(5-methylcytosin-1-yl)-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane

(1R,3R,4R,7S)-7-benzyloxy-1-(4,4'-dimethoxytrityl)oxymethyl-3-(4-N-benzoyl-5-methylcytosin-1-yl)-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane

(1R,3R,4R,7S)-7-benzyloxy-1-(4,4'-dimethoxytrityl)oxymethyl-3-(4-N-acetyl-5-methylcytosin-1-yl)-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane