Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

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Chemical Name:Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester
CAS No.:314038-30-7
Molecular Formula:C₂₁H₂₄Cl₃NO₉
Molecular Weight:540.782
Hs Code.:

Synonyms:Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

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Chemical Property of Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

There total 3 articles about Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl 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: 77.0%

: 545-06-2
trichloroacetonitrile

: 39686-94-7,56632-47-4,65827-58-9,99202-62-7,99202-66-1,103082-79-7,103703-00-0,103703-01-1,118711-49-2,127853-23-0,139563-66-9
1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose

: 314038-30-7
Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: 1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose; With ammonia; In tetrahydrofuran; methanol; at 20 ℃; for 4h; Inert atmosphere;

trichloroacetonitrile; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 3h;
DOI:10.1021/acs.orglett.0c04026

Reference yield:

: 18685-18-2
3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose

: 314038-30-7
Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: water / 4 h / 70 °C

1.2: 5 h / 110 °C

2.1: ammonia / tetrahydrofuran; methanol / 4 h / 20 °C / Inert atmosphere

2.2: 3 h / 0 °C

With ammonia; water; In tetrahydrofuran; methanol;
DOI:10.1021/acs.orglett.0c04026

Reference yield:

: 100-39-0
benzyl bromide

: 314038-30-7
Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0 °C / Inert atmosphere

1.2: 2 h / 0 - 20 °C / Inert atmosphere

2.1: water / 4 h / 70 °C

2.2: 5 h / 110 °C

3.1: ammonia / tetrahydrofuran; methanol / 4 h / 20 °C / Inert atmosphere

3.2: 3 h / 0 °C

With ammonia; water; sodium hydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/acs.orglett.0c04026