methyl (6R)-2,6-anhydro-3,4-di-O-benzyl-5-deoxy-6-(dimethoxyphosphoryl)-5-nitro-D-gluconate

Base Information

Chemical Name:methyl (6R)-2,6-anhydro-3,4-di-O-benzyl-5-deoxy-6-(dimethoxyphosphoryl)-5-nitro-D-gluconate
CAS No.:1295541-47-7
Molecular Formula:C₂₃H₂₈NO₁₀P
Molecular Weight:509.45
Hs Code.:

Synonyms:

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Chemical Property of methyl (6R)-2,6-anhydro-3,4-di-O-benzyl-5-deoxy-6-(dimethoxyphosphoryl)-5-nitro-D-gluconate

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Technology Process of methyl (6R)-2,6-anhydro-3,4-di-O-benzyl-5-deoxy-6-(dimethoxyphosphoryl)-5-nitro-D-gluconate

There total 5 articles about methyl (6R)-2,6-anhydro-3,4-di-O-benzyl-5-deoxy-6-(dimethoxyphosphoryl)-5-nitro-D-gluconate 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: 35.0%

: 1295541-45-5
methyl 2,6-anhydro-3,4-di-O-benzyl-5-deoxy-5-nitro-D-lyxohex-5-enonate

: 868-85-9
Dimethyl phosphite

: 1295541-47-7
methyl (6R)-2,6-anhydro-3,4-di-O-benzyl-5-deoxy-6-(dimethoxyphosphoryl)-5-nitro-D-gluconate

Guidance literature:: With triethylamine; In tetrahydrofuran; at 20 ℃; for 48h; Inert atmosphere;
DOI:10.1021/jo2002193

Reference yield:

: 3,4-di-O-benzyl-D-glucuronal

: 1295541-47-7
methyl (6R)-2,6-anhydro-3,4-di-O-benzyl-5-deoxy-6-(dimethoxyphosphoryl)-5-nitro-D-gluconate

Guidance literature:: Multi-step reaction with 3 steps

1.1: potassium hydrogencarbonate / N,N-dimethyl-formamide / 3 h / 20 °C

2.1: nitro acetate / water / 1.5 h / -33 °C / Cooling with acetone-dry ice; Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

3.1: triethylamine / tetrahydrofuran / 48 h / 20 °C / Inert atmosphere

With nitro acetate; potassium hydrogencarbonate; triethylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide;
DOI:10.1021/jo2002193

Reference yield:

: 207564-33-8
(2S,3S,4R)-3,4-Bis-benzyloxy-3,4-dihydro-2H-pyran-2-carbaldehyde

: 1295541-47-7
methyl (6R)-2,6-anhydro-3,4-di-O-benzyl-5-deoxy-6-(dimethoxyphosphoryl)-5-nitro-D-gluconate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium dihydrogenphosphate; sodium hypochlorite; 2-methyl-but-2-ene; sodium chloride / water; tert-butyl alcohol / 2 h / 20 °C

2.1: potassium hydrogencarbonate / N,N-dimethyl-formamide / 3 h / 20 °C

3.1: nitro acetate / water / 1.5 h / -33 °C / Cooling with acetone-dry ice; Inert atmosphere

3.2: 0 - 20 °C / Inert atmosphere

4.1: triethylamine / tetrahydrofuran / 48 h / 20 °C / Inert atmosphere

With sodium hypochlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; nitro acetate; potassium hydrogencarbonate; triethylamine; sodium chloride; In tetrahydrofuran; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jo2002193