dimethyl 2-(5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-(benzyloxymethyl)-1-O-(tert-butyl(dimethyl)silyl)-3,5-dideoxy-D-erythro-L-gluco-nonitol-2-C-yl)ethylphosphonate

Base Information

Chemical Name:dimethyl 2-(5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-(benzyloxymethyl)-1-O-(tert-butyl(dimethyl)silyl)-3,5-dideoxy-D-erythro-L-gluco-nonitol-2-C-yl)ethylphosphonate
CAS No.:869550-14-1
Molecular Formula:C₅₃H₇₆NO₁₄PSi
Molecular Weight:1010.24
Hs Code.:

dimethyl 2-(5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-(benzyloxymethyl)-1-O-(tert-butyl(dimethyl)silyl)-3,5-dideoxy-D-erythro-L-gluco-nonitol-2-C-yl)ethylphosphonate

Synonyms:dimethyl 2-(5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-(benzyloxymethyl)-1-O-(tert-butyl(dimethyl)silyl)-3,5-dideoxy-D-erythro-L-gluco-nonitol-2-C-yl)ethylphosphonate

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Chemical Property of dimethyl 2-(5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-(benzyloxymethyl)-1-O-(tert-butyl(dimethyl)silyl)-3,5-dideoxy-D-erythro-L-gluco-nonitol-2-C-yl)ethylphosphonate

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Technology Process of dimethyl 2-(5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-(benzyloxymethyl)-1-O-(tert-butyl(dimethyl)silyl)-3,5-dideoxy-D-erythro-L-gluco-nonitol-2-C-yl)ethylphosphonate

There total 7 articles about dimethyl 2-(5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-(benzyloxymethyl)-1-O-(tert-butyl(dimethyl)silyl)-3,5-dideoxy-D-erythro-L-gluco-nonitol-2-C-yl)ethylphosphonate 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: 75.0%

: 934390-47-3
dimethyl 2-(5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-(benzyloxymethyl)-1-O-(tert-butyl(dimethyl)silyl)-3,5-dideoxy-D-erythro-L-gluco-nonitol-2-C-yl)-1-((phenoxythiocarbonyl)oxyethyl)phosphonate

: 869550-14-1
dimethyl 2-(5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-(benzyloxymethyl)-1-O-(tert-butyl(dimethyl)silyl)-3,5-dideoxy-D-erythro-L-gluco-nonitol-2-C-yl)ethylphosphonate

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 70 ℃; for 2h;
DOI:10.1021/jo0512608

Reference yield:

: 869550-11-8
5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-(benzyloxymethyl)-3,5-dideoxy-2-C-(2-propenyl)-D-erythro-L-gluco-nonitol

: 869550-14-1
dimethyl 2-(5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-(benzyloxymethyl)-1-O-(tert-butyl(dimethyl)silyl)-3,5-dideoxy-D-erythro-L-gluco-nonitol-2-C-yl)ethylphosphonate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 93 percent / imidazole / dimethylformamide / 0 - 20 °C

2.1: O₃ / methanol; CH₂Cl₂ / 0.33 h / -78 °C

2.2: 92 percent / Me₂S / methanol; CH₂Cl₂ / -78 - 20 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -78 °C

3.2: 86 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.1: 75 percent / n-Bu₃SnH; AIBN / toluene / 2 h / 70 °C

With 1H-imidazole; n-butyllithium; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; ozone; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo0512608

Reference yield:

: 869550-10-7
methyl 5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-benzyloxymethyl-3,5-dideoxy-2-C-(2-propenyl)-D-erythro-L-gluco-nononate

: 869550-14-1
dimethyl 2-(5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-(benzyloxymethyl)-1-O-(tert-butyl(dimethyl)silyl)-3,5-dideoxy-D-erythro-L-gluco-nonitol-2-C-yl)ethylphosphonate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 98 percent / LiEt₃BH / tetrahydrofuran / 0.5 h / 20 °C

2.1: 93 percent / imidazole / dimethylformamide / 0 - 20 °C

3.1: O₃ / methanol; CH₂Cl₂ / 0.33 h / -78 °C

3.2: 92 percent / Me₂S / methanol; CH₂Cl₂ / -78 - 20 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -78 °C

4.2: 86 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.1: 75 percent / n-Bu₃SnH; AIBN / toluene / 2 h / 70 °C

With 1H-imidazole; n-butyllithium; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; lithium triethylborohydride; ozone; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo0512608