2,2,2-Trichloro-acetimidic acid (2S,4aR,6R,7R,8R,8aR)-7-acetylamino-2-phenyl-6-(2,2,2-trichloro-acetimidoyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Base Information

• Chemical Name: 2,2,2-Trichloro-acetimidic acid (2S,4aR,6R,7R,8R,8aR)-7-acetylamino-2-phenyl-6-(2,2,2-trichloro-acetimidoyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
• CAS No.: 188245-67-2
• Molecular Formula: C₁₉H₁₉Cl₆N₃O₆
• Molecular Weight: 598.094

Synonyms:2,2,2-Trichloro-acetimidic acid (2S,4aR,6R,7R,8R,8aR)-7-acetylamino-2-phenyl-6-(2,2,2-trichloro-acetimidoyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Chemical Property of 2,2,2-Trichloro-acetimidic acid (2S,4aR,6R,7R,8R,8aR)-7-acetylamino-2-phenyl-6-(2,2,2-trichloro-acetimidoyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

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Technology Process of 2,2,2-Trichloro-acetimidic acid (2S,4aR,6R,7R,8R,8aR)-7-acetylamino-2-phenyl-6-(2,2,2-trichloro-acetimidoyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

There total 1 articles about 2,2,2-Trichloro-acetimidic acid (2S,4aR,6R,7R,8R,8aR)-7-acetylamino-2-phenyl-6-(2,2,2-trichloro-acetimidoyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-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: 60.0%

trichloroacetonitrile (545-06-2) + N-((2S,4aR,6S,7R,8R,8aR)-6,8-Dihydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide (172139-01-4) → 2,2,2-Trichloro-acetimidic acid (2S,4aR,6R,7R,8R,8aR)-7-acetylamino-2-phenyl-6-(2,2,2-trichloro-acetimidoyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (188245-67-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at -20 ℃;

DOI:10.1016/S0040-4039(96)02490-2

Reference yield: 68.0%

N-Fmoc serine phenacyl ester (125760-26-1) + 2,2,2-Trichloro-acetimidic acid (2S,4aR,6R,7R,8R,8aR)-7-acetylamino-2-phenyl-6-(2,2,2-trichloro-acetimidoyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (188245-67-2) → (S)-3-[(2S,4aR,6S,7R,8R,8aR)-7-Acetylamino-2-phenyl-8-(2,2,2-trichloro-acetimidoyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester (188245-68-3)

Guidance literature:

With boron trifluoride diethyl etherate; In tetrahydrofuran; at -20 ℃;

DOI:10.1016/S0040-4039(96)02490-2

Reference yield: 35.0%

2,2,2-Trichloro-acetimidic acid (2S,4aR,6R,7R,8R,8aR)-7-acetylamino-2-phenyl-6-(2,2,2-trichloro-acetimidoyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (188245-67-2) + (2S,3R)-3-((2S,4aR,6S,7R,8R,8aR)-7-Acetylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid 2-oxo-2-phenyl-ethyl ester (188245-71-8) → C59H59Cl3N4O16

Guidance literature:

With boron trifluoride diethyl etherate; In tetrahydrofuran; at -20 ℃;

DOI:10.1016/S0040-4039(96)02490-2

upstream raw materials:

trichloroacetonitrile

N-((2S,4aR,6S,7R,8R,8aR)-6,8-Dihydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide

Downstream raw materials:

(S)-3-[(2S,4aR,6S,7R,8R,8aR)-7-Acetylamino-2-phenyl-8-(2,2,2-trichloro-acetimidoyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester

(2S,3R)-3-[(2S,4aR,6S,7R,8R,8aR)-7-Acetylamino-2-phenyl-8-(2,2,2-trichloro-acetimidoyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid 2-oxo-2-phenyl-ethyl ester

(S)-3-((2S,4aR,6S,7R,8R,8aR)-7-Acetylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester

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