(1R,2R)-1-O-[2-N-(tert-butoxycarbonyl)amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl]-cyclohexanediol

Base Information

• Chemical Name: (1R,2R)-1-O-[2-N-(tert-butoxycarbonyl)amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl]-cyclohexanediol
• CAS No.: 1574348-20-1
• Molecular Formula: C₃₈H₄₉NO₈
• Molecular Weight: 647.809

Synonyms:(1R,2R)-1-O-[2-N-(tert-butoxycarbonyl)amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl]-cyclohexanediol

Chemical Property of (1R,2R)-1-O-[2-N-(tert-butoxycarbonyl)amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl]-cyclohexanediol

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of (1R,2R)-1-O-[2-N-(tert-butoxycarbonyl)amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl]-cyclohexanediol

There total 8 articles about (1R,2R)-1-O-[2-N-(tert-butoxycarbonyl)amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl]-cyclohexanediol 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: 60.0%

(1R,2R)-1-O-[2-N-(tert-butoxycarbonyl)amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl]-2-O-(tert-butyldimethylsilyl)cyclohexanediol (1574348-19-8) → (1R,2R)-1-O-[2-N-(tert-butoxycarbonyl)amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl]-cyclohexanediol (1574348-20-1)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 96h; Inert atmosphere;

DOI:10.1039/c3ob42164c

Reference yield:

(1R,2R)-1-O-(2-azido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)cyclohexanediol (1574347-73-1) → (1R,2R)-1-O-[2-N-(tert-butoxycarbonyl)amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl]-cyclohexanediol (1574348-20-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

2.1: sodium methylate; methanol / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere

3.2: 24 h / 20 °C / Inert atmosphere

4.1: triphenylphosphine / tetrahydrofuran; water / 3 h / 60 °C / Inert atmosphere

5.1: ethyl acetate / 24 h / 20 °C / Inert atmosphere

6.1: pyridine hydrogenfluoride / tetrahydrofuran / 96 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; methanol; sodium methylate; sodium hydride; pyridine hydrogenfluoride; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; mineral oil;

DOI:10.1039/c3ob42164c

Reference yield:

3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranosyl trichloroacetimidate (145840-43-3) → (1R,2R)-1-O-[2-N-(tert-butoxycarbonyl)amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl]-cyclohexanediol (1574348-20-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: trimethylsilyl trifluoromethanesulfonate / diethyl ether; dichloromethane / 2 h / 20 °C / Molecular sieve; Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

3.1: sodium methylate; methanol / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere

4.2: 24 h / 20 °C / Inert atmosphere

5.1: triphenylphosphine / tetrahydrofuran; water / 3 h / 60 °C / Inert atmosphere

6.1: ethyl acetate / 24 h / 20 °C / Inert atmosphere

7.1: pyridine hydrogenfluoride / tetrahydrofuran / 96 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; methanol; trimethylsilyl trifluoromethanesulfonate; sodium methylate; sodium hydride; pyridine hydrogenfluoride; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; mineral oil;

DOI:10.1039/c3ob42164c

upstream raw materials:

(1R,2R)-1-O-(2-azido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)cyclohexanediol

3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranosyl trichloroacetimidate

(1R,2R)-trans-1,2-cyclohexanediol

1R,2R-1-O-(2-azido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-O-(tertbutyldimethylsilyl)-cyclohexanediol

Downstream raw materials:

triethylammonium (1R,2R)-1-O-[2-N-(tert-butoxycarbonyl)-amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl]cyclohexanediol 2-(1,2-di-O-hexadecanoyl-sn-glycerol3-phosphate)

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