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

Base Information

• Chemical Name: 1,5-anhydro-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-2-nitro-D-arabino-hex-1-enitol
• CAS No.: 944065-07-0
• Molecular Formula: C₂₆H₃₅NO₆Si
• Molecular Weight: 485.653

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

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

Chemical Property:

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

There total 2 articles about 1,5-anhydro-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-2-nitro-D-arabino-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:

tert-butyldimethylsilyl chloride (18162-48-6) → 1,5-anhydro-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-2-nitro-D-arabino-hex-1-enitol (944065-07-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 84 percent / imidazole / dimethylformamide / 12 h / 20 °C

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

2.2: 54 percent / triethylamine / CH₂Cl₂ / 0.42 h

With 1H-imidazole; nitric acid; acetic anhydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo061670b

Reference yield:

3,6-di-O-benzyl-D-glucal (145852-76-2) → 1,5-anhydro-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-2-nitro-D-arabino-hex-1-enitol (944065-07-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 84 percent / imidazole / dimethylformamide / 12 h / 20 °C

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

2.2: 54 percent / triethylamine / CH₂Cl₂ / 0.42 h

With 1H-imidazole; nitric acid; acetic anhydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo061670b

Reference yield: 63.0%

1,5-anhydro-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-2-nitro-D-arabino-hex-1-enitol (944065-07-0) + 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-D-lyxo-hex-1-enitol (944065-09-2)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/jo061670b

upstream raw materials:

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

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-D-lyxo-hex-1-enitol

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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