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

Base Information

• Chemical Name: (3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)nona-1,8-diene
• CAS No.: 1184705-79-0
• Molecular Formula: C₃₈H₄₁NO₄
• Molecular Weight: 575.748

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

Chemical Property of (3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)nona-1,8-diene

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)nona-1,8-diene

There total 10 articles about (3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)nona-1,8-diene 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: 93.0%

(3R,4R,6S)-6-(benzylamino)-3,4-bis(benzyloxy)nona-1,8-diene (1184705-85-8) + benzyl chloroformate (501-53-1,94274-21-2) → (3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)nona-1,8-diene (1184705-79-0)

Guidance literature:

With potassium hydrogencarbonate; In dichloromethane; water; at 0 - 20 ℃; for 2.16667h;

DOI:10.1002/ejoc.200900310

Reference yield:

methyl-alpha-D-glucopyranoside (97-30-3) → (3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)nona-1,8-diene (1184705-79-0)

Guidance literature:

Multi-step reaction with 10 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

With pyridine; 1H-imidazole; 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

Reference yield:

methyl 3,4-di-O-benzyl-6-O-trityl-α-D-glucopyranoside (1184705-42-7) → (3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)nona-1,8-diene (1184705-79-0)

Guidance literature:

Multi-step reaction with 6 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

With 1H-imidazole; 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

upstream raw materials:

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

benzyl chloroformate

methyl 3,4-di-O-benzyl-6-O-trityl-α-D-glucopyranoside

methyl 3,4-di-O-benzyl-2-O-(methylsulfanylthiocarbonyl)-6-O-trityl-α-D-glucopyranoside

Downstream raw materials:

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

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