(-)-(3S,5R)-N-(1-{4-[dimethyl-(1,1,2-trimethylpropyl)-silanyloxymethyl]-3-formyl-cyclopent-2-enyl}-2'-oxo-1',2'-dihydro-pyrimidin-4'-yl)-benzamide

Base Information

Chemical Name:(-)-(3S,5R)-N-(1-{4-[dimethyl-(1,1,2-trimethylpropyl)-silanyloxymethyl]-3-formyl-cyclopent-2-enyl}-2'-oxo-1',2'-dihydro-pyrimidin-4'-yl)-benzamide
CAS No.:737004-01-2
Molecular Formula:C₂₆H₃₅N₃O₄Si
Molecular Weight:481.667
Hs Code.:

Synonyms:(-)-(3S,5R)-N-(1-{4-[dimethyl-(1,1,2-trimethylpropyl)-silanyloxymethyl]-3-formyl-cyclopent-2-enyl}-2'-oxo-1',2'-dihydro-pyrimidin-4'-yl)-benzamide

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Chemical Property of (-)-(3S,5R)-N-(1-{4-[dimethyl-(1,1,2-trimethylpropyl)-silanyloxymethyl]-3-formyl-cyclopent-2-enyl}-2'-oxo-1',2'-dihydro-pyrimidin-4'-yl)-benzamide

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Technology Process of (-)-(3S,5R)-N-(1-{4-[dimethyl-(1,1,2-trimethylpropyl)-silanyloxymethyl]-3-formyl-cyclopent-2-enyl}-2'-oxo-1',2'-dihydro-pyrimidin-4'-yl)-benzamide

There total 5 articles about (-)-(3S,5R)-N-(1-{4-[dimethyl-(1,1,2-trimethylpropyl)-silanyloxymethyl]-3-formyl-cyclopent-2-enyl}-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:

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

: 737004-01-2
(-)-(3S,5R)-N-(1-{4-[dimethyl-(1,1,2-trimethylpropyl)-silanyloxymethyl]-3-formyl-cyclopent-2-enyl}-2'-oxo-1',2'-dihydro-pyrimidin-4'-yl)-benzamide

Guidance literature:: Multi-step reaction with 4 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

3.1: PPTS / acetone / 3 h / Heating

4.1: 316 mg / pyridine / 16 h / 20 °C

With pyridine; dmap; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; In dichloromethane; dimethyl sulfoxide; acetone;
DOI:10.1002/chem.200400079

Reference yield:

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

: 737004-01-2
(-)-(3S,5R)-N-(1-{4-[dimethyl-(1,1,2-trimethylpropyl)-silanyloxymethyl]-3-formyl-cyclopent-2-enyl}-2'-oxo-1',2'-dihydro-pyrimidin-4'-yl)-benzamide

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 65 percent / PPh₃ / [Pd(PPh₃)4] / dimethylsulfoxide; tetrahydrofuran / 16 h / 70 °C

2.1: PPTS / acetone / 3 h / Heating

3.1: 316 mg / pyridine / 16 h / 20 °C

With pyridine; pyridinium p-toluenesulfonate; sodium hydride; In dimethyl sulfoxide; acetone;
DOI:10.1002/chem.200400079

Reference yield:

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

: 737004-01-2
(-)-(3S,5R)-N-(1-{4-[dimethyl-(1,1,2-trimethylpropyl)-silanyloxymethyl]-3-formyl-cyclopent-2-enyl}-2'-oxo-1',2'-dihydro-pyrimidin-4'-yl)-benzamide

Guidance literature:: Multi-step reaction with 5 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

4.1: PPTS / acetone / 3 h / Heating

5.1: 316 mg / pyridine / 16 h / 20 °C

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