benzyl 2-O-acetyl-4,5,7,8-tetrakis-O-(chloroacetyl)-3-deoxy-D-manno-2-octulopyranosonate

Base Information

Chemical Name:benzyl 2-O-acetyl-4,5,7,8-tetrakis-O-(chloroacetyl)-3-deoxy-D-manno-2-octulopyranosonate
CAS No.:121700-63-8
Molecular Formula:C₂₅H₂₆Cl₄O₁₃
Molecular Weight:676.286
Hs Code.:

Synonyms:benzyl 2-O-acetyl-4,5,7,8-tetrakis-O-(chloroacetyl)-3-deoxy-D-manno-2-octulopyranosonate

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Chemical Property of benzyl 2-O-acetyl-4,5,7,8-tetrakis-O-(chloroacetyl)-3-deoxy-D-manno-2-octulopyranosonate

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Technology Process of benzyl 2-O-acetyl-4,5,7,8-tetrakis-O-(chloroacetyl)-3-deoxy-D-manno-2-octulopyranosonate

There total 7 articles about benzyl 2-O-acetyl-4,5,7,8-tetrakis-O-(chloroacetyl)-3-deoxy-D-manno-2-octulopyranosonate 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%

: 115848-15-2,115848-16-3
benzyl 4,5,7,8-tetrakis-O-(chloroacetyl)-3-deoxy-D-manno-2-octulosonate

: 75-36-5
acetyl chloride

: 121700-63-8
benzyl 2-O-acetyl-4,5,7,8-tetrakis-O-(chloroacetyl)-3-deoxy-D-manno-2-octulopyranosonate

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃;
DOI:10.1016/0008-6215(88)85041-9

Reference yield:

: 100-39-0
benzyl bromide

: 121700-63-8
benzyl 2-O-acetyl-4,5,7,8-tetrakis-O-(chloroacetyl)-3-deoxy-D-manno-2-octulopyranosonate

Guidance literature:: Multi-step reaction with 4 steps

1: 0.9 g / K₂CO₃ / dimethylformamide / 12 h / Ambient temperature

2: 0.52 g / 2,6-lutidine / CH₂Cl₂; triethylamine / 1.) 0 deg C, 2.) 20 deg C, 18 h

3: 90 percent / 42percent tetrafluoroboric acid / acetonitrile; H₂O / 0.25 h / Ambient temperature

4: 86 percent / 2,6-lutidine / CH₂Cl₂ / 20 °C

With 2,6-dimethylpyridine; tetrafluoroboric acid; potassium carbonate; In dichloromethane; water; triethylamine; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/0008-6215(88)85041-9

Reference yield:

: 118542-36-2,118542-49-7,121700-59-2
(4R,5R,6R)-6-((R)-1,2-Dihydroxy-ethyl)-4,5-dihydroxy-2-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

: 121700-63-8
benzyl 2-O-acetyl-4,5,7,8-tetrakis-O-(chloroacetyl)-3-deoxy-D-manno-2-octulopyranosonate

Guidance literature:: Multi-step reaction with 5 steps

1: 0.2M KOH / dioxane / 1 h / Ambient temperature

2: 0.9 g / K₂CO₃ / dimethylformamide / 12 h / Ambient temperature

3: 0.52 g / 2,6-lutidine / CH₂Cl₂; triethylamine / 1.) 0 deg C, 2.) 20 deg C, 18 h

4: 90 percent / 42percent tetrafluoroboric acid / acetonitrile; H₂O / 0.25 h / Ambient temperature

5: 86 percent / 2,6-lutidine / CH₂Cl₂ / 20 °C

With 2,6-dimethylpyridine; potassium hydroxide; tetrafluoroboric acid; potassium carbonate; In 1,4-dioxane; dichloromethane; water; triethylamine; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/0008-6215(88)85041-9