(2S)-N-[(2-allyloxycarbonylamino)-4-benzyloxy-5-methoxybenzoyl]-2-(tert-butyldimethylsilyloxymethyl)-4-(2-hydroxyethyl)-2,3-dihydropyrrole

Base Information

Chemical Name:(2S)-N-[(2-allyloxycarbonylamino)-4-benzyloxy-5-methoxybenzoyl]-2-(tert-butyldimethylsilyloxymethyl)-4-(2-hydroxyethyl)-2,3-dihydropyrrole
CAS No.:260417-81-0
Molecular Formula:C₃₂H₄₄N₂O₇Si
Molecular Weight:596.796
Hs Code.:

Synonyms:(2S)-N-[(2-allyloxycarbonylamino)-4-benzyloxy-5-methoxybenzoyl]-2-(tert-butyldimethylsilyloxymethyl)-4-(2-hydroxyethyl)-2,3-dihydropyrrole

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Chemical Property of (2S)-N-[(2-allyloxycarbonylamino)-4-benzyloxy-5-methoxybenzoyl]-2-(tert-butyldimethylsilyloxymethyl)-4-(2-hydroxyethyl)-2,3-dihydropyrrole

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Technology Process of (2S)-N-[(2-allyloxycarbonylamino)-4-benzyloxy-5-methoxybenzoyl]-2-(tert-butyldimethylsilyloxymethyl)-4-(2-hydroxyethyl)-2,3-dihydropyrrole

There total 2 articles about (2S)-N-[(2-allyloxycarbonylamino)-4-benzyloxy-5-methoxybenzoyl]-2-(tert-butyldimethylsilyloxymethyl)-4-(2-hydroxyethyl)-2,3-dihydropyrrole 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: 55.0%

: 260417-80-9
(2S)-N-[(2-allyloxycarbonylamino)-4-benzyloxy-5-methoxybenzoyl]-2-(tert-butyldimethylsilyloxymethyl)-4-(methoxycarbonylmethyl)-2,3-dihydropyrrole

: 260417-81-0
(2S)-N-[(2-allyloxycarbonylamino)-4-benzyloxy-5-methoxybenzoyl]-2-(tert-butyldimethylsilyloxymethyl)-4-(2-hydroxyethyl)-2,3-dihydropyrrole

Guidance literature:: With lithium borohydride; In tetrahydrofuran; at 0 ℃;
DOI:10.1016/S0960-894X(00)00351-6

Reference yield:

: 260417-69-4
{5-benzyloxy-2-[2-(tert-butyl-dimethyl-silanyloxymethyl)-4-oxo-pyrrolidine-1-carbonyl]-4-methoxy-phenyl}-carbamic acid allyl ester

: 260417-81-0
(2S)-N-[(2-allyloxycarbonylamino)-4-benzyloxy-5-methoxybenzoyl]-2-(tert-butyldimethylsilyloxymethyl)-4-(2-hydroxyethyl)-2,3-dihydropyrrole

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / NaH / tetrahydrofuran / 0 °C

2: 55 percent / LiBH₄ / tetrahydrofuran / 0 °C

With lithium borohydride; sodium hydride; In tetrahydrofuran; 1: Condensation / 2: Reduction;
DOI:10.1016/S0960-894X(00)00351-6

Reference yield:

: 260417-81-0
(2S)-N-[(2-allyloxycarbonylamino)-4-benzyloxy-5-methoxybenzoyl]-2-(tert-butyldimethylsilyloxymethyl)-4-(2-hydroxyethyl)-2,3-dihydropyrrole

: 260543-56-4
(11aS)-8-benzyloxy-2-(2-hydroxyethyl)-7-methoxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one

Guidance literature:: Multi-step reaction with 5 steps

1: 58 percent / pyridine / 25 °C

2: 81 percent / AcOH / tetrahydrofuran; H₂O

3: 82 percent / (COCl₂)2; DMSO; TEA / CH₂Cl₂ / -45 °C

4: 78 percent / aq. K₂CO₃ / methanol; CH₂Cl₂

5: 100 percent / Pd(Ph₃)4; PPh₃; pyrrolidine / CH₂Cl₂

With pyrrolidine; pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; (COCl₂)2; TEA; potassium carbonate; acetic acid; dimethyl sulfoxide; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; 1: Acetylation / 2: desilylation / 3: Cyclization / 4: Deacetylation / 5: Elimination;
DOI:10.1016/S0960-894X(00)00351-6