(3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)cycloheptene

Base Information

Chemical Name:(3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)cycloheptene
CAS No.:1184705-82-5
Molecular Formula:C₃₆H₃₇NO₄
Molecular Weight:547.694
Hs Code.:

Synonyms:(3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)cycloheptene

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Chemical Property of (3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)cycloheptene

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Technology Process of (3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)cycloheptene

There total 11 articles about (3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)cycloheptene 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: 97.0%

: 1184705-79-0
(3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)nona-1,8-diene

: 1184705-82-5
(3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)cycloheptene

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 20 ℃; for 36h; Inert atmosphere; Darkness;
DOI:10.1002/ejoc.200900310

Reference yield:

: 1184705-42-7
methyl 3,4-di-O-benzyl-6-O-trityl-α-D-glucopyranoside

: 1184705-82-5
(3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)cycloheptene

Guidance literature:: Multi-step reaction with 7 steps

1.1: 1H-imidazole; sodium hydride / tetrahydrofuran / 3.5 h / 20 °C / Inert atmosphere

1.2: 1.5 h / 20 °C / Inert atmosphere

2.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 7 h / 110 °C / Inert atmosphere

3.1: methanol; sulfuric acid / 2.5 h / 20 °C / Inert atmosphere

4.1: 1H-imidazole; triphenylphosphine / toluene / Co-concentrating

4.2: 67 °C / Inert atmosphere

5.1: chloro-trimethyl-silane; zinc / tetrahydrofuran / 1.25 h / 40 °C / Inert atmosphere; Sonication

5.2: 0.75 h / 40 °C / Inert atmosphere

5.3: 2 h / 40 °C / Inert atmosphere; Sonication

6.1: potassium hydrogencarbonate / dichloromethane; water / 2.17 h / 0 - 20 °C

7.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 36 h / 20 °C / Inert atmosphere; Darkness

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; methanol; chloro-trimethyl-silane; 2,2'-azobis(isobutyronitrile); sulfuric acid; tri-n-butyl-tin hydride; sodium hydride; potassium hydrogencarbonate; triphenylphosphine; zinc; In tetrahydrofuran; dichloromethane; water; toluene;
DOI:10.1002/ejoc.200900310

Reference yield:

: 97-30-3
methyl-alpha-D-glucopyranoside

: 1184705-82-5
(3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)cycloheptene

Guidance literature:: Multi-step reaction with 11 steps

1.1: pyridine / 3 h / 90 °C

2.1: tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide / acetonitrile / 16 h / 82 °C / Soxhlet apparatus; Molecular sieve

3.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide / 0 °C

3.2: 0 - 20 °C

4.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2.5 h / 20 °C / Inert atmosphere

5.1: 1H-imidazole; sodium hydride / tetrahydrofuran / 3.5 h / 20 °C / Inert atmosphere

5.2: 1.5 h / 20 °C / Inert atmosphere

6.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 7 h / 110 °C / Inert atmosphere

7.1: methanol; sulfuric acid / 2.5 h / 20 °C / Inert atmosphere

8.1: 1H-imidazole; triphenylphosphine / toluene / Co-concentrating

8.2: 67 °C / Inert atmosphere

9.1: chloro-trimethyl-silane; zinc / tetrahydrofuran / 1.25 h / 40 °C / Inert atmosphere; Sonication

9.2: 0.75 h / 40 °C / Inert atmosphere

9.3: 2 h / 40 °C / Inert atmosphere; Sonication

10.1: potassium hydrogencarbonate / dichloromethane; water / 2.17 h / 0 - 20 °C

11.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 36 h / 20 °C / Inert atmosphere; Darkness

With pyridine; 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; methanol; chloro-trimethyl-silane; 2,2'-azobis(isobutyronitrile); sulfuric acid; water; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; potassium hydrogencarbonate; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1002/ejoc.200900310