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

Base Information

• Chemical Name: (3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)cycloheptanone
• CAS No.: 1184705-74-5
• Molecular Formula: C₃₆H₃₇NO₅
• Molecular Weight: 563.693
• Mol file: 1184705-74-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 18 articles about (3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)cycloheptanone 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: 50.0%

(3R,4R,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)cycloheptene (1184705-68-7) → (3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)cycloheptanone (1184705-74-5) + (2S,3R,5R)-5-[(benzyl)(benzyloxycarbonyl)amino]-2,3-bis(benzyloxy)cycloheptanone (1184705-70-1)

Guidance literature:

(3R,4R,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)cycloheptene; With borane-THF; In tetrahydrofuran; at -40 - 20 ℃; Inert atmosphere;

With water; dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1002/ejoc.200900310

Reference yield:

methyl 2-O-(p-methoxybenzyl)-6-O-trityl-α-D-glucopyranoside (214068-17-4) → (3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)cycloheptanone (1184705-74-5) + (2S,3R,5R)-5-[(benzyl)(benzyloxycarbonyl)amino]-2,3-bis(benzyloxy)cycloheptanone (1184705-70-1)

Guidance literature:

Multi-step reaction with 10 steps

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

1.2: 0 - 20 °C

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

3.1: 1H-imidazole; sodium hydride / tetrahydrofuran / 3.5 h / 20 °C / Inert atmosphere

3.2: 1.5 h / 20 °C / Inert atmosphere

4.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 7 h / 110 °C / Inert atmosphere

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

6.1: 1H-imidazole; triphenylphosphine / toluene / Co-concentrating

6.2: 67 °C / Inert atmosphere

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

7.2: 0.75 h / 40 °C / Inert atmosphere

7.3: 2 h / 40 °C / Inert atmosphere; Sonication

8.1: potassium hydrogencarbonate / dichloromethane; water / 1.5 h / 0 - 20 °C

9.1: 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

10.1: borane-THF / tetrahydrofuran / -40 - 20 °C / Inert atmosphere

10.2: 1 h / 20 °C / Inert atmosphere

10.3: 1 h / 20 °C

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; methanol; chloro-trimethyl-silane; borane-THF; 2,2'-azobis(isobutyronitrile); sulfuric acid; water; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium hydrogencarbonate; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; 10.3: Dess-Martin oxidation;

DOI:10.1002/ejoc.200900310

Reference yield:

methyl 3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-6-O-trityl-α-D-glucopyranoside → (3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)cycloheptanone (1184705-74-5) + (2S,3R,5R)-5-[(benzyl)(benzyloxycarbonyl)amino]-2,3-bis(benzyloxy)cycloheptanone (1184705-70-1)

Guidance literature:

Multi-step reaction with 9 steps

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

2.1: 1H-imidazole; sodium hydride / tetrahydrofuran / 3.5 h / 20 °C / Inert atmosphere

2.2: 1.5 h / 20 °C / Inert atmosphere

3.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 7 h / 110 °C / Inert atmosphere

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

5.1: 1H-imidazole; triphenylphosphine / toluene / Co-concentrating

5.2: 67 °C / Inert atmosphere

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

6.2: 0.75 h / 40 °C / Inert atmosphere

6.3: 2 h / 40 °C / Inert atmosphere; Sonication

7.1: potassium hydrogencarbonate / dichloromethane; water / 1.5 h / 0 - 20 °C

8.1: 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

9.1: borane-THF / tetrahydrofuran / -40 - 20 °C / Inert atmosphere

9.2: 1 h / 20 °C / Inert atmosphere

9.3: 1 h / 20 °C

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; methanol; chloro-trimethyl-silane; borane-THF; 2,2'-azobis(isobutyronitrile); sulfuric acid; water; tri-n-butyl-tin hydride; sodium hydride; potassium hydrogencarbonate; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; In tetrahydrofuran; dichloromethane; water; toluene; 9.3: Dess-Martin oxidation;

DOI:10.1002/ejoc.200900310

upstream raw materials:

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

(3R,4R,6R)-6-(benzylamino)-3,4-bis(benzyloxy)nona-1,8-diene

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

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