2,2,2-Trichloro-acetimidic acid (2R,3S,4R,5R,6S)-5-azido-4-benzyloxy-3-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: 2,2,2-Trichloro-acetimidic acid (2R,3S,4R,5R,6S)-5-azido-4-benzyloxy-3-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 1053555-47-7
• Molecular Formula: C₂₁H₂₁Cl₃N₄O₄S
• Molecular Weight: 531.847
• Mol file: 1053555-47-7.mol

Synonyms:

Chemical Property of 2,2,2-Trichloro-acetimidic acid (2R,3S,4R,5R,6S)-5-azido-4-benzyloxy-3-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2,2-Trichloro-acetimidic acid (2R,3S,4R,5R,6S)-5-azido-4-benzyloxy-3-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

There total 1 articles about 2,2,2-Trichloro-acetimidic acid (2R,3S,4R,5R,6S)-5-azido-4-benzyloxy-3-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl 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:

trichloroacetonitrile (545-06-2) + phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside (666753-83-9) → 2,2,2-Trichloro-acetimidic acid (2R,3S,4R,5R,6S)-5-azido-4-benzyloxy-3-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester (1053555-47-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 0.75h;

DOI:10.1039/b309823k

Reference yield:

trifluoromethylsulfonic anhydride (358-23-6) + 2,2,2-Trichloro-acetimidic acid (2R,3S,4R,5R,6S)-5-azido-4-benzyloxy-3-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester (1053555-47-7) → 2,2,2-Trichloro-acetimidic acid (2R,3S,4R,5R,6S)-5-azido-4-benzyloxy-6-phenylsulfanyl-3-trifluoromethanesulfonyloxy-tetrahydro-pyran-2-ylmethyl ester (1053256-69-1)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 0.0833333h;

DOI:10.1039/b309823k

Reference yield:

2,2,2-Trichloro-acetimidic acid (2R,3S,4R,5R,6S)-5-azido-4-benzyloxy-3-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester (1053555-47-7) → ((2S,3R,4S,5R,6S)-3-Amino-5-azido-4-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-yl)-methanol

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / CH₂Cl₂ / 0.08 h / 0 °C

2: 4.16 g / (i-Pr)2NEt / CH₂Cl₂ / 3.5 h / 0 °C

3: aq. AcOH / 0.5 h / 20 °C

With pyridine; acetic acid; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1039/b309823k

upstream raw materials:

trichloroacetonitrile

phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside

Downstream raw materials:

2,2,2-Trichloro-acetimidic acid (2R,3S,4R,5R,6S)-5-azido-4-benzyloxy-6-phenylsulfanyl-3-trifluoromethanesulfonyloxy-tetrahydro-pyran-2-ylmethyl ester

(4aS,6S,7R,8S,8aR)-7-Azido-8-benzyloxy-6-phenylsulfanyl-2-trichloromethyl-4,4a,6,7,8,8a-hexahydro-pyrano[3,2-d][1,3]oxazine

phenyl 4-(N-benzyloxycarbonyl)-amino-2-azido-3-O-benzyl-2,4-dideoxy-1-thio-β-D-galactopyranoside

phenyl 6-O-acetyl-4-(N-benzyloxycarbonyl)-amino-2-azido-3-O-benzyl-2,4-dideoxy-1-thio-β-D-galactopyranoside