(2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester
• CAS No.: 154397-04-3
• Molecular Formula: C₂₁H₂₂Cl₃NO₁₀
• Molecular Weight: 554.765

Synonyms:(2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Chemical Property of (2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of (2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester

There total 4 articles about (2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester 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: 92.0%

trichloroacetonitrile (545-06-2) + (2S,3S,4S,5S)-3,4,5-Triacetoxy-6-hydroxy-tetrahydro-pyran-2-carboxylic acid benzyl ester → (2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester (154397-04-3)

Guidance literature:

With sodium carbonate; In dichloromethane;

DOI:10.1021/jo00081a004

Reference yield:

1,2,3,4-tetra-O-acetyl-D-mannopyranoside (51008-88-9) → (2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester (154397-04-3)

Guidance literature:

Multi-step reaction with 4 steps

1: RuCl₃*3H₂O, NaIO₄ / CCl₄; H₂O; acetonitrile

2: NaHCO₃ / dimethylformamide

3: 94 percent / 2-aminoethanol / ethyl acetate; dimethylsulfoxide

4: 92 percent / Na₂CO₃ / CH₂Cl₂

With ruthenium trichloride; sodium periodate; sodium hydrogencarbonate; sodium carbonate; ethanolamine; In tetrachloromethane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00081a004

Reference yield:

(2S,3S,4S,5S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid → (2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester (154397-04-3)

Guidance literature:

Multi-step reaction with 3 steps

1: NaHCO₃ / dimethylformamide

2: 94 percent / 2-aminoethanol / ethyl acetate; dimethylsulfoxide

3: 92 percent / Na₂CO₃ / CH₂Cl₂

With sodium hydrogencarbonate; sodium carbonate; ethanolamine; In dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00081a004

upstream raw materials:

trichloroacetonitrile

1,2,3,4-tetra-O-acetyl-D-mannopyranoside

Downstream raw materials:

(2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-{(R)-carboxy-[(2S,3R,4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-methoxy-tetrahydro-furan-2-yl]-methoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester

(2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-{(R)-carbamoyl-[(2S,3R,4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-methoxy-tetrahydro-furan-2-yl]-methoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester

(2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-{(S)-1-[(2R,3R,4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-methoxy-tetrahydro-furan-2-yl]-2-hydroxy-ethoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester

(4S,5S,6S)-4,5-Diacetoxy-6-{(R)-carbamoyl-[(2S,3R,4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-methoxy-tetrahydro-furan-2-yl]-methoxy}-5,6-dihydro-4H-pyran-2-carboxylic acid benzyl ester

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