Trifluoro-methanesulfonic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methylsulfanyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Base Information

• Chemical Name: Trifluoro-methanesulfonic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methylsulfanyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester
• CAS No.: 208048-06-0
• Molecular Formula: C₄₉H₅₁F₃O₁₂S₂
• Molecular Weight: 953.064

Synonyms:

Chemical Property of Trifluoro-methanesulfonic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methylsulfanyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Trifluoro-methanesulfonic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methylsulfanyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

There total 7 articles about Trifluoro-methanesulfonic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methylsulfanyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-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:

trifluoromethylsulfonic anhydride (358-23-6) + (2R,4aR,6S,7R,8R,8aR)-8-Benzyloxy-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methylsulfanyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (208048-05-9) → Trifluoro-methanesulfonic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methylsulfanyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (208048-06-0)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 11h;

DOI:10.1039/a709293h

Reference yield:

benzyl bromide (100-39-0) → Trifluoro-methanesulfonic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methylsulfanyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (208048-06-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 55 percent / NaH, CuCl₂ / dimethylformamide / 1.) r.t., 2 h, 2.) r.t., 42 h

2: 88 percent / pyridine / 3 h / 0 °C

3: molecular sieves 4 Angstroem, Br₂ / CH₂Cl₂ / 0.3 h / 0 °C

4: 2,6-di-tert-butyl-4-methylpyridine, silver triflate / CH₂Cl₂; toluene / 1.) -40 deg C, 30 min, 2.) -40 to -50 deg C, 40 min

5: 96 percent / NaOMe / dioxane; methanol / 2.75 h / 40 °C

6: pyridine / CH₂Cl₂ / 11 h / 0 °C

With pyridine; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; bromine; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; copper dichloride; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1039/a709293h

Reference yield:

methyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside → Trifluoro-methanesulfonic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methylsulfanyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (208048-06-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 55 percent / NaH, CuCl₂ / dimethylformamide / 1.) r.t., 2 h, 2.) r.t., 42 h

2: 88 percent / pyridine / 3 h / 0 °C

3: molecular sieves 4 Angstroem, Br₂ / CH₂Cl₂ / 0.3 h / 0 °C

4: 2,6-di-tert-butyl-4-methylpyridine, silver triflate / CH₂Cl₂; toluene / 1.) -40 deg C, 30 min, 2.) -40 to -50 deg C, 40 min

5: 96 percent / NaOMe / dioxane; methanol / 2.75 h / 40 °C

6: pyridine / CH₂Cl₂ / 11 h / 0 °C

With pyridine; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; bromine; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; copper dichloride; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1039/a709293h

upstream raw materials:

trifluoromethylsulfonic anhydride

(2R,4aR,6S,7R,8R,8aR)-8-Benzyloxy-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methylsulfanyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

benzyl bromide

methyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

Downstream raw materials:

methyl 4-O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-mannopyranosyl)-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

(2R,3S,4R,5S,6S)-5-Azido-4-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methylsulfanyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-ol

methyl 4-O-(4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-mannopyranosyl)-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

C₇₄H₈₃NO₁₆

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