Acetic acid (2S,3R,4S,5S,6R)-5-acetoxy-2-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-octyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-6-cyanomethoxymethyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5S,6R)-5-acetoxy-2-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-octyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-6-cyanomethoxymethyl-tetrahydro-pyran-3-yl ester
• CAS No.: 196876-53-6
• Molecular Formula: C₄₉H₆₄N₂O₁₃
• Molecular Weight: 889.053
• Mol file: 196876-53-6.mol

Synonyms:Acetic acid (2S,3R,4S,5S,6R)-5-acetoxy-2-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-octyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-6-cyanomethoxymethyl-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3R,4S,5S,6R)-5-acetoxy-2-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-octyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-6-cyanomethoxymethyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3R,4S,5S,6R)-5-acetoxy-2-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-octyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-6-cyanomethoxymethyl-tetrahydro-pyran-3-yl ester

There total 8 articles about Acetic acid (2S,3R,4S,5S,6R)-5-acetoxy-2-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-octyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-6-cyanomethoxymethyl-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: 67.0%

phenyl 2,4-di-O-acetyl-3-O-benzyl-6-O-cyanomethyl-1-thio-β-D-galactopyranoside (196876-48-9) + octyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (196876-45-6) → Acetic acid (2S,3R,4S,5S,6R)-5-acetoxy-2-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-octyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-6-cyanomethoxymethyl-tetrahydro-pyran-3-yl ester (196876-53-6)

Guidance literature:

With 4 A molecular sieve; bromine; silver trifluoromethanesulfonate; In dichloromethane; at -30 ℃; for 1h;

DOI:10.1016/S0008-6215(97)00142-0

Reference yield:

1-thiophenyl-β-D-galactopyranoside (16758-34-2) → Acetic acid (2S,3R,4S,5S,6R)-5-acetoxy-2-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-octyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-6-cyanomethoxymethyl-tetrahydro-pyran-3-yl ester (196876-53-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Bu₂SnO, 2.) Bu₄NI / 1.) benzene, reflux, 24 h, 2.) 65 deg C, overnight.

2: lp

3: 67 percent / AgOTf, molecular sieves 4 Angstroem, Br₂ / CH₂Cl₂ / 1 h / -30 °C

With 4 A molecular sieve; bromine; silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; In dichloromethane;

DOI:10.1016/S0008-6215(97)00142-0

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → Acetic acid (2S,3R,4S,5S,6R)-5-acetoxy-2-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-octyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-6-cyanomethoxymethyl-tetrahydro-pyran-3-yl ester (196876-53-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / p-TsOH*H₂O / acetonitrile / Ambient temperature

2: 86 percent / NaH / dimethylformamide / 0 °C

3: 70 percent / NaCNBH₃, molecular sieves 4 Angstroem, HCl / tetrahydrofuran; diethyl ether / 1.) -5 deg C, 2 h, 2.) room temperatuere, overnight.

4: 67 percent / AgOTf, molecular sieves 4 Angstroem, Br₂ / CH₂Cl₂ / 1 h / -30 °C

With hydrogenchloride; 4 A molecular sieve; bromine; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0008-6215(97)00142-0

upstream raw materials:

phenyl 2,4-di-O-acetyl-3-O-benzyl-6-O-cyanomethyl-1-thio-β-D-galactopyranoside

octyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

1-thiophenyl-β-D-galactopyranoside

benzaldehyde dimethyl acetal