2,2,2-Trichloro-acetimidic acid (3R,4S,6R)-5-[(E)-benzyloxyimino]-3-{(2S,4S,5S)-5-[ethyl-(9H-fluoren-9-ylmethoxycarbonyl)-amino]-4-methoxy-tetrahydro-pyran-2-yloxy}-6-methyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl ester

Base Information

• Chemical Name: 2,2,2-Trichloro-acetimidic acid (3R,4S,6R)-5-[(E)-benzyloxyimino]-3-{(2S,4S,5S)-5-[ethyl-(9H-fluoren-9-ylmethoxycarbonyl)-amino]-4-methoxy-tetrahydro-pyran-2-yloxy}-6-methyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl ester
• CAS No.: 148152-88-9
• Molecular Formula: C₄₄H₅₆Cl₃N₃O₉Si
• Molecular Weight: 905.388
• Mol file: 148152-88-9.mol

Synonyms:2,2,2-Trichloro-acetimidic acid (3R,4S,6R)-5-[(E)-benzyloxyimino]-3-{(2S,4S,5S)-5-[ethyl-(9H-fluoren-9-ylmethoxycarbonyl)-amino]-4-methoxy-tetrahydro-pyran-2-yloxy}-6-methyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl ester

Chemical Property of 2,2,2-Trichloro-acetimidic acid (3R,4S,6R)-5-[(E)-benzyloxyimino]-3-{(2S,4S,5S)-5-[ethyl-(9H-fluoren-9-ylmethoxycarbonyl)-amino]-4-methoxy-tetrahydro-pyran-2-yloxy}-6-methyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2,2-Trichloro-acetimidic acid (3R,4S,6R)-5-[(E)-benzyloxyimino]-3-{(2S,4S,5S)-5-[ethyl-(9H-fluoren-9-ylmethoxycarbonyl)-amino]-4-methoxy-tetrahydro-pyran-2-yloxy}-6-methyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl ester

There total 13 articles about 2,2,2-Trichloro-acetimidic acid (3R,4S,6R)-5-[(E)-benzyloxyimino]-3-{(2S,4S,5S)-5-[ethyl-(9H-fluoren-9-ylmethoxycarbonyl)-amino]-4-methoxy-tetrahydro-pyran-2-yloxy}-6-methyl-4-triethylsilanyloxy-tetrahydro-pyran-2-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: 98.0%

((3S,4S,6S)-6-{(3R,4S,6R)-5-[(E)-Benzyloxyimino]-2-hydroxy-6-methyl-4-triethylsilanyloxy-tetrahydro-pyran-3-yloxy}-4-methoxy-tetrahydro-pyran-3-yl)-ethyl-carbamic acid 9H-fluoren-9-ylmethyl ester (132958-86-2) + trichloroacetonitrile (545-06-2) → 2,2,2-Trichloro-acetimidic acid (3R,4S,6R)-5-[(E)-benzyloxyimino]-3-{(2S,4S,5S)-5-[ethyl-(9H-fluoren-9-ylmethoxycarbonyl)-amino]-4-methoxy-tetrahydro-pyran-2-yloxy}-6-methyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl ester (148152-88-9)

Guidance literature:

With sodium hydride; In dichloromethane; at 25 ℃; for 2h;

Reference yield:

D-Fucose (73-34-7,87-96-7,488-79-9,551-63-3,609-01-8,643-17-4,643-18-5,4164-09-4,6014-42-2,6155-36-8,6189-71-5,6696-41-9,6736-43-2,13224-93-6,22611-09-2,28161-49-1,28161-50-4,28161-52-6,45864-36-6,63814-64-2,71116-59-1,71116-61-5,72598-05-1,87936-88-7,87936-89-8,97466-79-0,116908-82-8,120442-60-6,123484-22-0,133576-32-6) → 2,2,2-Trichloro-acetimidic acid (3R,4S,6R)-5-[(E)-benzyloxyimino]-3-{(2S,4S,5S)-5-[ethyl-(9H-fluoren-9-ylmethoxycarbonyl)-amino]-4-methoxy-tetrahydro-pyran-2-yloxy}-6-methyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl ester (148152-88-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 98 percent / NEt₃, 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 - 25 °C

2: 30percent HBr, acetic acid / 0.5 h / 0 °C

3: AgCO₃ / CH₂Cl₂ / 16 h / 25 °C / 3 Angstroem-Molekularsieb

4: 95 percent / NaOMe, MeOH / 3 h / 25 °C

5: 90 percent / acetonitrile / 2 h / Heating

6: AgClO₄, SnCl₂ / tetrahydrofuran / 6 h / -90 - -10 deg C

7: 90 percent / NaH, ethanediol / tetrahydrofuran / 0.5 h / 0 °C

8: 1) n-Bu₂SnO, 2) Br₂, n-Bu₃SnOMe / 1) MeOH, 1h, reflux, 2) CH₂Cl₂, 2h, 25 deg C

9: 90 percent / pyridinium-p-toluenesulfonate / benzene / 0.5 h / 25 °C

10: 98 percent / 2,6-Lutidin / CH₂Cl₂ / 0.5 h / 0 °C

11: 95 percent / tetrahydrofuran; H₂O / 0.25 h / 0 °C / Irradiation

12: 98 percent / NaH / CH₂Cl₂ / 2 h / 25 °C

With 2,6-dimethylpyridine; methanol; dmap; silver (II) carbonate; hydrogen bromide; bromine; sodium methylate; tributyltin methoxide; silver perchlorate; pyridinium p-toluenesulfonate; sodium hydride; di(n-butyl)tin oxide; ethylene glycol; acetic acid; triethylamine; tin(ll) chloride; In tetrahydrofuran; dichloromethane; water; acetonitrile; benzene;

Reference yield:

N-benzyloxyamine (622-33-3) → 2,2,2-Trichloro-acetimidic acid (3R,4S,6R)-5-[(E)-benzyloxyimino]-3-{(2S,4S,5S)-5-[ethyl-(9H-fluoren-9-ylmethoxycarbonyl)-amino]-4-methoxy-tetrahydro-pyran-2-yloxy}-6-methyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl ester (148152-88-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / pyridinium-p-toluenesulfonate / benzene / 0.5 h / 25 °C

2: 98 percent / 2,6-Lutidin / CH₂Cl₂ / 0.5 h / 0 °C

3: 95 percent / tetrahydrofuran; H₂O / 0.25 h / 0 °C / Irradiation

4: 98 percent / NaH / CH₂Cl₂ / 2 h / 25 °C

With 2,6-dimethylpyridine; pyridinium p-toluenesulfonate; sodium hydride; In tetrahydrofuran; dichloromethane; water; benzene;

upstream raw materials:

((3S,4S,6S)-6-{(3R,4S,6R)-5-[(E)-Benzyloxyimino]-2-hydroxy-6-methyl-4-triethylsilanyloxy-tetrahydro-pyran-3-yloxy}-4-methoxy-tetrahydro-pyran-3-yl)-ethyl-carbamic acid 9H-fluoren-9-ylmethyl ester

trichloroacetonitrile

D-Fucose

N-benzyloxyamine

Downstream raw materials:

((3S,4S,6S)-6-{(2R,3R,4S,6R)-2-Benzyloxy-5-[(E)-benzyloxyimino]-6-methyl-4-triethylsilanyloxy-tetrahydro-pyran-3-yloxy}-4-methoxy-tetrahydro-pyran-3-yl)-ethyl-carbamic acid 9H-fluoren-9-ylmethyl ester

((3S,4S,6S)-6-{(2S,3R,4S,6R)-2-Benzyloxy-5-[(E)-benzyloxyimino]-6-methyl-4-triethylsilanyloxy-tetrahydro-pyran-3-yloxy}-4-methoxy-tetrahydro-pyran-3-yl)-ethyl-carbamic acid 9H-fluoren-9-ylmethyl ester

C₇₀H₇₇N₃O₁₃Si

C₇₀H₇₇N₃O₁₃Si