(3R,4R,5S,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)-5-hydroxycycloheptene

Base Information

Chemical Name:(3R,4R,5S,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)-5-hydroxycycloheptene
CAS No.:1184705-64-3
Molecular Formula:C₃₆H₃₇NO₅
Molecular Weight:563.693
Hs Code.:

Synonyms:(3R,4R,5S,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)-5-hydroxycycloheptene

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Chemical Property of (3R,4R,5S,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)-5-hydroxycycloheptene

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Technology Process of (3R,4R,5S,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)-5-hydroxycycloheptene

There total 9 articles about (3R,4R,5S,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)-5-hydroxycycloheptene 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: 99.0%

: 1184705-61-0
(3R,4S,5S,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)-5-(p-methoxybenzyloxy)cycloheptene

: 1184705-64-3
(3R,4R,5S,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)-5-hydroxycycloheptene

Guidance literature:: With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 2.5h;
DOI:10.1002/ejoc.200900310

Reference yield:

: 1184705-55-2
(3R,4S,5S,6R)-6-(benzylamino)-3,4-bis(benzyloxy)-5-(p-methoxybenzyloxy)nona-1,8-diene

: 1184705-64-3
(3R,4R,5S,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)-5-hydroxycycloheptene

Guidance literature:: Multi-step reaction with 3 steps

1: potassium hydrogencarbonate / dichloromethane; water / 2 h / 0 - 20 °C

2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 48 h / 20 °C / Inert atmosphere; Darkness

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

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; water; potassium hydrogencarbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;
DOI:10.1002/ejoc.200900310

Reference yield:

: 1184705-54-1
methyl 3,4-di-O-benzyl-6-deoxy-6-iodo-2-O-(p-methoxybenzyl)-α-D-glucopyranoside

: 1184705-64-3
(3R,4R,5S,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)-5-hydroxycycloheptene

Guidance literature:: Multi-step reaction with 4 steps

1.1: chloro-trimethyl-silane; zinc / tetrahydrofuran / 40 °C / Sonication

1.2: 1 h / 40 °C

1.3: 1.42 h / 40 °C / Sonication

2.1: potassium hydrogencarbonate / dichloromethane; water / 2 h / 0 - 20 °C

3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 48 h / 20 °C / Inert atmosphere; Darkness

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

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; chloro-trimethyl-silane; water; potassium hydrogencarbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; In tetrahydrofuran; dichloromethane; water;
DOI:10.1002/ejoc.200900310