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

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Chemical Name:(3R,4S,5S,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)-5-[(methylsulfanyl)thiocarbonyloxy]cycloheptene
CAS No.:1184705-66-5
Molecular Formula:C₃₈H₃₉NO₅S₂
Molecular Weight:653.863
Hs Code.:

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

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

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

There total 10 articles about (3R,4S,5S,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)-5-[(methylsulfanyl)thiocarbonyloxy]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: 78.0%

: 75-15-0,12122-00-8
carbon disulfide

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

: 74-88-4
methyl iodide

: 1184705-66-5
(3R,4S,5S,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)-5-[(methylsulfanyl)thiocarbonyloxy]cycloheptene

Guidance literature:: carbon disulfide; (3R,4R,5S,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)-5-hydroxycycloheptene; With 1H-imidazole; sodium hydride; In tetrahydrofuran; at 20 ℃; for 4.25h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; at 20 ℃; Inert atmosphere;
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

: 1184705-66-5
(3R,4S,5S,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)-5-[(methylsulfanyl)thiocarbonyloxy]cycloheptene

Guidance literature:: Multi-step reaction with 5 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

5.1: 1H-imidazole; sodium hydride / tetrahydrofuran / 4.25 h / 20 °C / Inert atmosphere

5.2: 20 °C / Inert atmosphere

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; chloro-trimethyl-silane; water; sodium hydride; potassium hydrogencarbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; In tetrahydrofuran; dichloromethane; water;
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

: 1184705-66-5
(3R,4S,5S,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)-5-[(methylsulfanyl)thiocarbonyloxy]cycloheptene

Guidance literature:: Multi-step reaction with 4 steps

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

2.1: 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

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

4.1: 1H-imidazole; sodium hydride / tetrahydrofuran / 4.25 h / 20 °C / Inert atmosphere

4.2: 20 °C / Inert atmosphere

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