(2R,3R,4S,5S,6R)-2-(4-(3-(((3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)piperidin-1-yl)oxy)propyl)-1H-1,2,3-triazol-1-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Base Information

• Chemical Name: (2R,3R,4S,5S,6R)-2-(4-(3-(((3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)piperidin-1-yl)oxy)propyl)-1H-1,2,3-triazol-1-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• CAS No.: 1425378-04-6
• Molecular Formula: C₃₈H₄₈N₄O₉
• Molecular Weight: 704.821

Synonyms:(2R,3R,4S,5S,6R)-2-(4-(3-(((3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)piperidin-1-yl)oxy)propyl)-1H-1,2,3-triazol-1-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Chemical Property of (2R,3R,4S,5S,6R)-2-(4-(3-(((3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)piperidin-1-yl)oxy)propyl)-1H-1,2,3-triazol-1-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

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Technology Process of (2R,3R,4S,5S,6R)-2-(4-(3-(((3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)piperidin-1-yl)oxy)propyl)-1H-1,2,3-triazol-1-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

There total 14 articles about (2R,3R,4S,5S,6R)-2-(4-(3-(((3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)piperidin-1-yl)oxy)propyl)-1H-1,2,3-triazol-1-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 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%

D-glucopyranosyl azide (20379-59-3) + (3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-1-(pent-4-yn-1-yloxy)piperidine (1353742-34-3) → (2R,3R,4S,5S,6R)-2-(4-(3-(((3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)piperidin-1-yl)oxy)propyl)-1H-1,2,3-triazol-1-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (1425378-04-6)

Guidance literature:

With copper(II) sulfate; sodium L-ascorbate; In water; tert-butyl alcohol; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1002/chem.201202374

Reference yield:

5-(benzyloxymethyl)cyclopentadiene (39939-07-6) → (2R,3R,4S,5S,6R)-2-(4-(3-(((3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)piperidin-1-yl)oxy)propyl)-1H-1,2,3-triazol-1-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (1425378-04-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: L-diisopinocampheylborane / tetrahydrofuran / 72 h / -78 - -10 °C / Inert atmosphere

1.2: 24 h / 20 °C / Inert atmosphere

2.1: 3-chloro-benzenecarboperoxoic acid / water; dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere

3.1: triethylamine / tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere

4.1: boron trifluoride diethyl etherate / dichloromethane / 3 h / 20 °C / Inert atmosphere

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 18 h / 0 - 20 °C / Inert atmosphere

6.1: sodium hydride / methanol; N,N-dimethyl-formamide; mineral oil / 2 h / 20 °C / Inert atmosphere

6.2: Inert atmosphere; Cooling with ice

7.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide; water / acetone / 20 °C / Inert atmosphere

7.2: Inert atmosphere

8.1: methanol; tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere; Molecular sieve

9.1: sodium cyanoborohydride; acetic acid / 4 h / 20 °C / Inert atmosphere

10.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 4 h / 20 °C / Inert atmosphere

With osmium(VIII) oxide; boron trifluoride diethyl etherate; water; sodium hydride; sodium cyanoborohydride; copper(II) sulfate; acetic acid; 4-methylmorpholine N-oxide; sodium L-ascorbate; triethylamine; 3-chloro-benzenecarboperoxoic acid; L-diisopinocampheylborane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; mineral oil; tert-butyl alcohol;

DOI:10.1002/chem.201202374

Reference yield:

(1R,2S)-2-((benzyloxy)methyl)cyclopent-3-en-1-ol (188399-48-6) → (2R,3R,4S,5S,6R)-2-(4-(3-(((3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)piperidin-1-yl)oxy)propyl)-1H-1,2,3-triazol-1-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (1425378-04-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 3-chloro-benzenecarboperoxoic acid / water; dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere

2.1: triethylamine / tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere

3.1: boron trifluoride diethyl etherate / dichloromethane / 3 h / 20 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 18 h / 0 - 20 °C / Inert atmosphere

5.1: sodium hydride / methanol; N,N-dimethyl-formamide; mineral oil / 2 h / 20 °C / Inert atmosphere

5.2: Inert atmosphere; Cooling with ice

6.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide; water / acetone / 20 °C / Inert atmosphere

6.2: Inert atmosphere

7.1: methanol; tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere; Molecular sieve

8.1: sodium cyanoborohydride; acetic acid / 4 h / 20 °C / Inert atmosphere

9.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 4 h / 20 °C / Inert atmosphere

With osmium(VIII) oxide; boron trifluoride diethyl etherate; water; sodium hydride; sodium cyanoborohydride; copper(II) sulfate; acetic acid; 4-methylmorpholine N-oxide; sodium L-ascorbate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; mineral oil; tert-butyl alcohol;

DOI:10.1002/chem.201202374

upstream raw materials:

benzyl bromide

benzyl alcohol

5-(benzyloxymethyl)cyclopentadiene

D-glucopyranosyl azide

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