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

Base Information

Chemical Name:(1R,3R,4R,7R)-7-benzyloxy-1-(benzoyloxymethyl)-3-[3-(benzyloxymethyl)thymin-1-yl]-2-oxa-5-azabicyclo[2.2.1]heptane
CAS No.:861230-85-5
Molecular Formula:C₃₃H₃₃N₃O₇
Molecular Weight:583.641
Hs Code.:

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

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

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

There total 10 articles about (1R,3R,4R,7R)-7-benzyloxy-1-(benzoyloxymethyl)-3-[3-(benzyloxymethyl)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%

: 861230-84-4
(1R,3R,4R,7R)-7-benzyloxy-3-[3-(benzyloxymethyl)thymin-1-yl]-1-(methylsulfonyloxymethyl)-2-oxa-5-azabicyclo[2.2.1]heptane

: 532-32-1
sodium benzoate

: 861230-85-5
(1R,3R,4R,7R)-7-benzyloxy-1-(benzoyloxymethyl)-3-[3-(benzyloxymethyl)thymin-1-yl]-2-oxa-5-azabicyclo[2.2.1]heptane

Guidance literature:: With 15-crown-5; In N,N-dimethyl-formamide; at 120 ℃; for 24h;
DOI:10.1002/ejoc.200500023

Reference yield:

: 861230-81-1
1-[3-O-benzyl-5-O-(methylsulfonyl)-4-C-(methylsolfonyloxymethyl)-α-L-erythro-pentofuranosyl]-3-(benzyloxymethyl)thymine

: 861230-85-5
(1R,3R,4R,7R)-7-benzyloxy-1-(benzoyloxymethyl)-3-[3-(benzyloxymethyl)thymin-1-yl]-2-oxa-5-azabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 4 steps

1.1: 70 percent / DMAP; pyridine / CH₂Cl₂ / 4 h / 0 °C

2.1: 83 percent / NaN₃ / dimethylformamide / 18 h / 20 °C

3.1: triphenylphosphane; pyridine / 20 h / 20 °C

3.2: 99 percent / aq. NH₃ / pyridine / 24 h / 20 °C

4.1: 92 percent / 15-crown-5 / dimethylformamide / 24 h / 120 °C

With pyridine; dmap; sodium azide; 15-crown-5; triphenylphosphine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200500023

Reference yield:

: 861230-80-0
1-[3-O-benzyl-5-O-(methylsulfonyl)-4-C-(methylsolfonyloxymethyl)-α-L-threo-pentofuranosyl]-3-(benzyloxymethyl)thymine

: 861230-85-5
(1R,3R,4R,7R)-7-benzyloxy-1-(benzoyloxymethyl)-3-[3-(benzyloxymethyl)thymin-1-yl]-2-oxa-5-azabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 5 steps

1.1: DMAP; pyridine; trifluoromethanesulfonic anhydride / CH₂Cl₂ / 4 h / 0 °C

1.2: 72 percent / aq. NaHCO₃ / CH₂Cl₂ / 0 - 20 °C

2.1: 70 percent / DMAP; pyridine / CH₂Cl₂ / 4 h / 0 °C

3.1: 83 percent / NaN₃ / dimethylformamide / 18 h / 20 °C

4.1: triphenylphosphane; pyridine / 20 h / 20 °C

4.2: 99 percent / aq. NH₃ / pyridine / 24 h / 20 °C

5.1: 92 percent / 15-crown-5 / dimethylformamide / 24 h / 120 °C

With pyridine; dmap; sodium azide; 15-crown-5; trifluoromethanesulfonic acid anhydride; triphenylphosphine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200500023