Trifluoro-methanesulfonic acid (1R,2S,3S,4S,5R)-2-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester

Base Information

Chemical Name:Trifluoro-methanesulfonic acid (1R,2S,3S,4S,5R)-2-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester
CAS No.:1054657-43-0
Molecular Formula:C₃₇H₄₁F₃O₁₂S
Molecular Weight:766.787
Hs Code.:

Trifluoro-methanesulfonic acid (1R,2S,3S,4S,5R)-2-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester

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Chemical Property of Trifluoro-methanesulfonic acid (1R,2S,3S,4S,5R)-2-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester

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Technology Process of Trifluoro-methanesulfonic acid (1R,2S,3S,4S,5R)-2-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester

There total 8 articles about Trifluoro-methanesulfonic acid (1R,2S,3S,4S,5R)-2-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-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:

: 100-39-0
benzyl bromide

: 1054657-43-0
Trifluoro-methanesulfonic acid (1R,2S,3S,4S,5R)-2-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 83 percent / NaH / dimethylformamide / 1.) r.t., 1 h, 2.) r.t., 2 h

2: 92 percent / 80percent aq. AcOH / 2 h / 75 °C

3: pyridine / 1.5 h / -40 °C

With pyridine; sodium hydride; acetic acid; In N,N-dimethyl-formamide;
DOI:10.1021/jo00111a008

Reference yield:

: 5349-10-0
1,6-anhydro-2,3-O-endo-benzylidene-β-mannopyranose

: 1054657-43-0
Trifluoro-methanesulfonic acid (1R,2S,3S,4S,5R)-2-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 84 percent / trimethylsilyl triflate, 4 Angstroem molecular sieves / CH₂Cl₂ / 1.) -20 deg C, 2 h, 2.) -20 deg C to 0 deg C, 2 h

2: 99 percent / NaOMe / methanol / 2 h / Ambient temperature

3: 1.) dibutyltin oxide, N-methylimidazole, 3 Angstroem molecular sieves / 1.) CH₃CN, 80 deg C, 2 h, 2.) 80 deg C, 3 h

4: 83 percent / NaH / dimethylformamide / 1.) r.t., 1 h, 2.) r.t., 2 h

5: 92 percent / 80percent aq. AcOH / 2 h / 75 °C

6: pyridine / 1.5 h / -40 °C

With pyridine; 1-methyl-1H-imidazole; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; sodium methylate; sodium hydride; di(n-butyl)tin oxide; acetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00111a008

Reference yield:

: 162710-65-8
O-(β-D-Galactopyranosyl)-(1->4)-1,6-anhydro-2,3-O-endo/exo-benzylidene-β-D-mannopyranose

: 1054657-43-0
Trifluoro-methanesulfonic acid (1R,2S,3S,4S,5R)-2-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) dibutyltin oxide, N-methylimidazole, 3 Angstroem molecular sieves / 1.) CH₃CN, 80 deg C, 2 h, 2.) 80 deg C, 3 h

2: 83 percent / NaH / dimethylformamide / 1.) r.t., 1 h, 2.) r.t., 2 h

3: 92 percent / 80percent aq. AcOH / 2 h / 75 °C

4: pyridine / 1.5 h / -40 °C

With pyridine; 1-methyl-1H-imidazole; 3 A molecular sieve; sodium hydride; di(n-butyl)tin oxide; acetic acid; In N,N-dimethyl-formamide;
DOI:10.1021/jo00111a008