Trifluoro-methanesulfonic acid (2R,3S,4S,6R)-4-benzyloxy-6-(3-benzyloxy-propyl)-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Trifluoro-methanesulfonic acid (2R,3S,4S,6R)-4-benzyloxy-6-(3-benzyloxy-propyl)-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 736170-20-0
• Molecular Formula: C₃₅H₃₇F₃O₇S
• Molecular Weight: 658.736

Synonyms:Trifluoro-methanesulfonic acid (2R,3S,4S,6R)-4-benzyloxy-6-(3-benzyloxy-propyl)-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Trifluoro-methanesulfonic acid (2R,3S,4S,6R)-4-benzyloxy-6-(3-benzyloxy-propyl)-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of Trifluoro-methanesulfonic acid (2R,3S,4S,6R)-4-benzyloxy-6-(3-benzyloxy-propyl)-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester

There total 9 articles about Trifluoro-methanesulfonic acid (2R,3S,4S,6R)-4-benzyloxy-6-(3-benzyloxy-propyl)-3-(naphthalen-2-ylmethoxy)-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: 100.0%

trifluoromethylsulfonic anhydride (358-23-6) + [(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-methanol (736170-47-1) → Trifluoro-methanesulfonic acid (2R,3S,4S,6R)-4-benzyloxy-6-(3-benzyloxy-propyl)-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester (736170-20-0)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2004.05.020

Reference yield:

benzyl 3-(3-O-benzyl-2-deoxy-α-D-allopyranosyl)propyl ether (189347-91-9) → Trifluoro-methanesulfonic acid (2R,3S,4S,6R)-4-benzyloxy-6-(3-benzyloxy-propyl)-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester (736170-20-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 2.67 h / 23 °C

2: 100 percent / NaH; Bu₄NI / tetrahydrofuran / 14 h / 0 - 25 °C

3: 99 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

4: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

With 2,6-dimethylpyridine; dmap; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2004.05.020

Reference yield:

(2R,3S,4R,6R)-2-(acetoxymethyl)-6-allyltetrahydro-2H-pyran-3,4-diyldiacetate (82795-64-0) → Trifluoro-methanesulfonic acid (2R,3S,4S,6R)-4-benzyloxy-6-(3-benzyloxy-propyl)-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester (736170-20-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 88 percent / NaOMe / methanol / 3 h / 0 - 23 °C

2.1: 79 percent / TsOH*H₂O / benzene; dimethylformamide / 7 h / Heating

3.1: (COCl)2; DMSO / CH₂Cl₂ / 0.25 h / -78 °C

3.2: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h / -78 - 0 °C

4.1: 95 percent / K-Selectride / tetrahydrofuran / 1 h / -78 °C

5.1: 9-BBN / tetrahydrofuran / 1 h / 23 °C

5.2: TBHP; NaOH / tetrahydrofuran; H₂O / 0.67 h / 0 - 23 °C

6.1: t-BuOK; Bu₄NI / tetrahydrofuran / 4 h / 23 °C

7.1: 94 percent / HCl / tetrahydrofuran; H₂O / 10 h / 23 °C

8.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 2.67 h / 23 °C

9.1: 100 percent / NaH; Bu₄NI / tetrahydrofuran / 14 h / 0 - 25 °C

10.1: 99 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

11.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

With 2,6-dimethylpyridine; hydrogenchloride; dmap; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium tri-sec-butyl-borohydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; benzene; 3.1: Swern oxidation / 3.2: Swern oxidation;

DOI:10.1016/j.tetlet.2004.05.020

upstream raw materials:

trifluoromethylsulfonic anhydride

[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-methanol

benzyl 3-(3-O-benzyl-2-deoxy-α-D-allopyranosyl)propyl ether

(2R,3S,4R,6R)-2-(acetoxymethyl)-6-allyltetrahydro-2H-pyran-3,4-diyldiacetate

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