O-(3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-2-nitro-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-tert-butyldimethylsilyl-2-deoxy-2-nitro-D-lyxo-hex-1-enitol

Base Information

• Chemical Name: O-(3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-2-nitro-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-tert-butyldimethylsilyl-2-deoxy-2-nitro-D-lyxo-hex-1-enitol
• CAS No.: 944065-10-5
• Molecular Formula: C₄₄H₇₂N₂O₁₂Si₃
• Molecular Weight: 905.318

Synonyms:O-(3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-2-nitro-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-tert-butyldimethylsilyl-2-deoxy-2-nitro-D-lyxo-hex-1-enitol

Chemical Property of O-(3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-2-nitro-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-tert-butyldimethylsilyl-2-deoxy-2-nitro-D-lyxo-hex-1-enitol

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Technology Process of O-(3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-2-nitro-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-tert-butyldimethylsilyl-2-deoxy-2-nitro-D-lyxo-hex-1-enitol

There total 8 articles about O-(3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-2-nitro-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-tert-butyldimethylsilyl-2-deoxy-2-nitro-D-lyxo-hex-1-enitol 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:

1,5-anhydro-3,4-di-O-tert-butyldimethylsilyl-2-deoxy-D-lyxo-hex-1-enitol (944065-08-1) → O-(3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-2-nitro-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-tert-butyldimethylsilyl-2-deoxy-2-nitro-D-lyxo-hex-1-enitol (944065-10-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 63 percent / potassium tert-butoxide / tetrahydrofuran / 2 h / 20 °C

2.1: conc. nitric acid; acetic anhydride / CH₂Cl₂ / 1 h / -30 °C

2.2: 45 percent / triethylamine / CH₂Cl₂ / 0.42 h

With potassium tert-butylate; nitric acid; acetic anhydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo061670b

Reference yield:

3,4-di-O-tert-butyldimethylsilyl-6-O-pivaloyl-galactal → O-(3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-2-nitro-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-tert-butyldimethylsilyl-2-deoxy-2-nitro-D-lyxo-hex-1-enitol (944065-10-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 2.3 g / DIBAL-H / CH₂Cl₂ / -70 °C

2.1: 63 percent / potassium tert-butoxide / tetrahydrofuran / 2 h / 20 °C

3.1: conc. nitric acid; acetic anhydride / CH₂Cl₂ / 1 h / -30 °C

3.2: 45 percent / triethylamine / CH₂Cl₂ / 0.42 h

With potassium tert-butylate; nitric acid; acetic anhydride; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo061670b

Reference yield:

1,5-anhydro-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-2-nitro-D-arabino-hex-1-enitol (944065-07-0) → O-(3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-2-nitro-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-tert-butyldimethylsilyl-2-deoxy-2-nitro-D-lyxo-hex-1-enitol (944065-10-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 63 percent / potassium tert-butoxide / tetrahydrofuran / 2 h / 20 °C

2.1: conc. nitric acid; acetic anhydride / CH₂Cl₂ / 1 h / -30 °C

2.2: 45 percent / triethylamine / CH₂Cl₂ / 0.42 h

With potassium tert-butylate; nitric acid; acetic anhydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo061670b

upstream raw materials:

1,5-anhydro-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-2-nitro-D-arabino-hex-1-enitol

1,5-anhydro-3,4-di-O-tert-butyldimethylsilyl-2-deoxy-D-lyxo-hex-1-enitol

tert-butyldimethylsilyl chloride

3,6-di-O-benzyl-D-glucal

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