2,2,2-Trichloro-acetimidic acid (2S,3S,4R,5R,6S)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl ester

Base Information

• Chemical Name: 2,2,2-Trichloro-acetimidic acid (2S,3S,4R,5R,6S)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl ester
• CAS No.: 168319-51-5
• Molecular Formula: C₃₁H₃₂Cl₃NO₆
• Molecular Weight: 620.957
• Mol file: 168319-51-5.mol

Synonyms:2,2,2-Trichloro-acetimidic acid (2S,3S,4R,5R,6S)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl ester

Chemical Property of 2,2,2-Trichloro-acetimidic acid (2S,3S,4R,5R,6S)-6-allyloxy-3,4,5-tris-benzyloxy-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 (2S,3S,4R,5R,6S)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl ester

There total 8 articles about 2,2,2-Trichloro-acetimidic acid (2S,3S,4R,5R,6S)-6-allyloxy-3,4,5-tris-benzyloxy-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: 87.0%

trichloroacetonitrile (545-06-2) + Allyl(5S)-5-hydroxy-2,3,4-tri-O-benzyl-α-D-xylopyranoside (168319-50-4) → 2,2,2-Trichloro-acetimidic acid (2S,3S,4R,5R,6S)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl ester (168319-51-5)

Guidance literature:

With 1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine; In 1,2-dichloro-ethane; at -30 ℃; for 0.166667h;

DOI:10.1002/hlca.19960790703

Reference yield:

allyl 2,3,4-tri-O-benzyl-6-O-trityl-α-D-glucopyranoside (168608-17-1) → 2,2,2-Trichloro-acetimidic acid (2S,3S,4R,5R,6S)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl ester (168319-51-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / BF₃*OEt₂, Et₃SiH / acetonitrile; CH₂Cl₂ / 0.17 h / 0 °C

2: 1.) CrO₃, pyridine; 2.) Ac₂O / 1.) DMF, CH₂Cl₂, 23 degC, 30 min; 2.) DMF, CH₂Cl₂, 9 h

3: 99 percent / HCO₂H / 0.5 h / 23 °C

4: 71 percent / benzene; pyridine / 0.42 h / 60 °C

5: 98 percent / 20percent diisobutylaluminium hydride / CH₂Cl₂; toluene / 0.25 h / -78 °C

6: 87 percent / 7-methyl-1,5,7-triazabicyclo<4.4.0>dec-5-ene / 1,2-dichloro-ethane / 0.17 h / -30 °C

With pyridine; chromium(VI) oxide; triethylsilane; formic acid; boron trifluoride diethyl etherate; acetic anhydride; diisobutylaluminium hydride; 1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine; In pyridine; dichloromethane; 1,2-dichloro-ethane; toluene; acetonitrile; benzene;

DOI:10.1002/hlca.19960790703

Reference yield:

1-O-allyl-6-O-trityl-α-D-glucopyranoside (107242-80-8) → 2,2,2-Trichloro-acetimidic acid (2S,3S,4R,5R,6S)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl ester (168319-51-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / NaH, Bu₄NI / tetrahydrofuran / 23 degC, 10 min, reflux 24 h

2: 93 percent / BF₃*OEt₂, Et₃SiH / acetonitrile; CH₂Cl₂ / 0.17 h / 0 °C

3: 1.) CrO₃, pyridine; 2.) Ac₂O / 1.) DMF, CH₂Cl₂, 23 degC, 30 min; 2.) DMF, CH₂Cl₂, 9 h

4: 99 percent / HCO₂H / 0.5 h / 23 °C

5: 71 percent / benzene; pyridine / 0.42 h / 60 °C

6: 98 percent / 20percent diisobutylaluminium hydride / CH₂Cl₂; toluene / 0.25 h / -78 °C

7: 87 percent / 7-methyl-1,5,7-triazabicyclo<4.4.0>dec-5-ene / 1,2-dichloro-ethane / 0.17 h / -30 °C

With pyridine; chromium(VI) oxide; triethylsilane; formic acid; boron trifluoride diethyl etherate; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; 1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine; In tetrahydrofuran; pyridine; dichloromethane; 1,2-dichloro-ethane; toluene; acetonitrile; benzene;

DOI:10.1002/hlca.19960790703

upstream raw materials:

trichloroacetonitrile

Allyl(5S)-5-hydroxy-2,3,4-tri-O-benzyl-α-D-xylopyranoside

1-O-allyl-6-O-trityl-α-D-glucopyranoside

allyl 2,3,4-tri-O-benzyl-6-O-trityl-α-D-glucopyranoside