(+)-(3'S,5'R,8'S)-N-[1-(8'-allyloxy-7'-oxa-[3.3.0]-bicyclooct-1'-ene-3'-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide

Base Information

Chemical Name:(+)-(3'S,5'R,8'S)-N-[1-(8'-allyloxy-7'-oxa-[3.3.0]-bicyclooct-1'-ene-3'-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide
CAS No.:808752-78-5
Molecular Formula:C₂₁H₂₁N₃O₄
Molecular Weight:379.415
Hs Code.:

Synonyms:(+)-(3'S,5'R,8'S)-N-[1-(8'-allyloxy-7'-oxa-[3.3.0]-bicyclooct-1'-ene-3'-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide

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Chemical Property of (+)-(3'S,5'R,8'S)-N-[1-(8'-allyloxy-7'-oxa-[3.3.0]-bicyclooct-1'-ene-3'-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide

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Technology Process of (+)-(3'S,5'R,8'S)-N-[1-(8'-allyloxy-7'-oxa-[3.3.0]-bicyclooct-1'-ene-3'-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide

There total 3 articles about (+)-(3'S,5'R,8'S)-N-[1-(8'-allyloxy-7'-oxa-[3.3.0]-bicyclooct-1'-ene-3'-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide 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: 65.0%

: 808752-67-2
(+)-(3S,5R,8S)-acetic acid 8-allyloxy-7-oxa-[3.3.0]-bicyclooct-1-ene-3-yl ester

: 26661-13-2
4-N-benzoylcytosine

: 808752-78-5
(+)-(3'S,5'R,8'S)-N-[1-(8'-allyloxy-7'-oxa-[3.3.0]-bicyclooct-1'-ene-3'-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide

Guidance literature:: 4-N-benzoylcytosine; With sodium hydride; In dimethyl sulfoxide; at 70 ℃; for 0.5h;

(+)-(3S,5R,8S)-acetic acid 8-allyloxy-7-oxa-[3.3.0]-bicyclooct-1-ene-3-yl ester; With triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dimethyl sulfoxide; at 70 ℃; for 16h;
DOI:10.1002/chem.200400079

Reference yield:

: 808752-65-0
(+)-(3S,5R,8S)-8-allyloxy-7-oxa-[3.3.0]-bicyclooct-1-ene-3-ol

: 808752-78-5
(+)-(3'S,5'R,8'S)-N-[1-(8'-allyloxy-7'-oxa-[3.3.0]-bicyclooct-1'-ene-3'-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide

Guidance literature:: Multi-step reaction with 2 steps

1.1: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

2.1: NaH / dimethylsulfoxide / 0.5 h / 70 °C

2.2: 65 percent / PPh₃ / [Pd(PPh₃)4] / dimethylsulfoxide; tetrahydrofuran / 16 h / 70 °C

With dmap; sodium hydride; triethylamine; In dichloromethane; dimethyl sulfoxide;
DOI:10.1002/chem.200400079

Reference yield:

: (+)-(3S,5R,8S)-8-allyloxy-2-trimethylsilyl-7-oxa-[3.3.0]-bicyclooct-1-ene-3-ol

: 808752-78-5
(+)-(3'S,5'R,8'S)-N-[1-(8'-allyloxy-7'-oxa-[3.3.0]-bicyclooct-1'-ene-3'-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: 81 percent / aq. t-BuOK / dimethylsulfoxide / 0.5 h / 20 °C

2.1: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

3.1: NaH / dimethylsulfoxide / 0.5 h / 70 °C

3.2: 65 percent / PPh₃ / [Pd(PPh₃)4] / dimethylsulfoxide; tetrahydrofuran / 16 h / 70 °C

With dmap; potassium tert-butylate; sodium hydride; triethylamine; In dichloromethane; dimethyl sulfoxide;
DOI:10.1002/chem.200400079