(11S,11aS)-2-(2-acetyloxyethyl)-10-allyloxycarbonyl-8-benzyloxy-11-hydroxy-7-methoxy-1,10,11,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one

Base Information

Chemical Name:(11S,11aS)-2-(2-acetyloxyethyl)-10-allyloxycarbonyl-8-benzyloxy-11-hydroxy-7-methoxy-1,10,11,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one
CAS No.:260417-84-3
Molecular Formula:C₂₈H₃₀N₂O₈
Molecular Weight:522.555
Hs Code.:

(11S,11aS)-2-(2-acetyloxyethyl)-10-allyloxycarbonyl-8-benzyloxy-11-hydroxy-7-methoxy-1,10,11,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one

Synonyms:(11S,11aS)-2-(2-acetyloxyethyl)-10-allyloxycarbonyl-8-benzyloxy-11-hydroxy-7-methoxy-1,10,11,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one

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Chemical Property of (11S,11aS)-2-(2-acetyloxyethyl)-10-allyloxycarbonyl-8-benzyloxy-11-hydroxy-7-methoxy-1,10,11,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one

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Technology Process of (11S,11aS)-2-(2-acetyloxyethyl)-10-allyloxycarbonyl-8-benzyloxy-11-hydroxy-7-methoxy-1,10,11,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one

There total 5 articles about (11S,11aS)-2-(2-acetyloxyethyl)-10-allyloxycarbonyl-8-benzyloxy-11-hydroxy-7-methoxy-1,10,11,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one 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: 82.0%

: 260417-83-2
(2S)-N-[(2-allyloxycarbonylamino)-4-benzyloxy-5-methoxybenzoyl]-4-(2-acetyloxyethyl)-2-(hydroxymethyl)-2,3-dihydropyrrole

: 260417-84-3
(11S,11aS)-2-(2-acetyloxyethyl)-10-allyloxycarbonyl-8-benzyloxy-11-hydroxy-7-methoxy-1,10,11,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one

Guidance literature:: With (COCl₂)2; TEA; dimethyl sulfoxide; In dichloromethane; at -45 ℃;
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

: 260417-84-3
(11S,11aS)-2-(2-acetyloxyethyl)-10-allyloxycarbonyl-8-benzyloxy-11-hydroxy-7-methoxy-1,10,11,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one

Guidance literature:: Multi-step reaction with 5 steps

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

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

3: 58 percent / pyridine / 25 °C

4: 81 percent / AcOH / tetrahydrofuran; H₂O

5: 82 percent / (COCl₂)2; DMSO; TEA / CH₂Cl₂ / -45 °C

With pyridine; lithium borohydride; (COCl₂)2; TEA; sodium hydride; acetic acid; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; water; 1: Condensation / 2: Reduction / 3: Acetylation / 4: desilylation / 5: Cyclization;
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

: 260417-84-3
(11S,11aS)-2-(2-acetyloxyethyl)-10-allyloxycarbonyl-8-benzyloxy-11-hydroxy-7-methoxy-1,10,11,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one

Guidance literature:: Multi-step reaction with 3 steps

1: 58 percent / pyridine / 25 °C

2: 81 percent / AcOH / tetrahydrofuran; H₂O

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

With pyridine; (COCl₂)2; TEA; acetic acid; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; water; 1: Acetylation / 2: desilylation / 3: Cyclization;
DOI:10.1016/S0960-894X(00)00351-6