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

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)-1-((phenoxythiocarbonyl)oxyethyl)phosphonate
CAS No.:934390-47-3
Molecular Formula:C₆₀H₈₀NO₁₆PSSi
Molecular Weight:1162.42
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)-1-((phenoxythiocarbonyl)oxyethyl)phosphonate

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)-1-((phenoxythiocarbonyl)oxyethyl)phosphonate

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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)-1-((phenoxythiocarbonyl)oxyethyl)phosphonate

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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)-1-((phenoxythiocarbonyl)oxyethyl)phosphonate

There total 6 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)-1-((phenoxythiocarbonyl)oxyethyl)phosphonate 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: 86.0%

: 869550-13-0
6-acetamido-3,7-anhydro-5,8,9,10-tetra-O-(benzyloxymethyl)-3-C-((tert-butyl(dimethyl)silyl)oxymethyl)-2,4,6-trideoxy-D-erythro-L-manno-decose

: 96-36-6,868-85-9
methyl phosphite

: 1005-56-7
phenylcarbonochloridothioate

: 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

Guidance literature:: 6-acetamido-3,7-anhydro-5,8,9,10-tetra-O-(benzyloxymethyl)-3-C-((tert-butyl(dimethyl)silyl)oxymethyl)-2,4,6-trideoxy-D-erythro-L-manno-decose; methyl phosphite; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.0833333h;

phenylcarbonochloridothioate; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;
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

: 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

Guidance literature:: Multi-step reaction with 3 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

With 1H-imidazole; n-butyllithium; ozone; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
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

: 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

Guidance literature:: Multi-step reaction with 4 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

With 1H-imidazole; n-butyllithium; lithium triethylborohydride; ozone; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo0512608