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

Base Information

• Chemical Name: Trifluoro-methanesulfonic acid (2R,3S,4S,6R)-4-benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 189347-96-4
• Molecular Formula: C₃₀H₄₃F₃O₇SSi
• Molecular Weight: 632.814

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

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

Chemical Property:

Purity/Quality:

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

There total 10 articles about Trifluoro-methanesulfonic acid (2R,3S,4S,6R)-4-benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-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:

trifluoromethylsulfonic anhydride (358-23-6) + triethylsilyl trifluoromethyl sulfonate (79271-56-0) + 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-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester (189347-96-4)

Guidance literature:

With 2,6-dimethylpyridine; Yield given. Multistep reaction; 1.) CH₂Cl₂, -78 deg C_.;

DOI:10.1021/ja9701523

Reference yield:

(2R,3S,6R)-2-acetoxymethyl-6-allyl-3,6-dihydro-2H-pyran-3-yl acetate (82740-87-2) → Trifluoro-methanesulfonic acid (2R,3S,4S,6R)-4-benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester (189347-96-4)

Guidance literature:

Multi-step reaction with 9 steps

1: K₂CO₃ / methanol

2: 1.46 g / m-CPBA, Na₂HPO₄ / toluene / 2 h / 0 °C

3: 1.13 g / CSA / CH₂Cl₂ / 48 h / Ambient temperature

4: 95 percent / LiAlH₄ / diethyl ether / 1.5 h / Ambient temperature

5: 95 percent / NaH / dimethylformamide; paraffin / 3 h / Ambient temperature

6: 1.) 9-BBN-H, 2.) 3M NaOH, 30percent H₂O₂ / 1.) THF, room temperature, 4 h, 2.) room temperature, 1 h

7: 92 percent / NaH / dimethylformamide; paraffin / 3 h / Ambient temperature

8: 92 percent / conc.HCl / tetrahydrofuran; H₂O / 5 h / 40 °C

9: 1.) 2,6-lutidine / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) -78 deg C, 30 min

With 2,6-dimethylpyridine; hydrogenchloride; sodium hydroxide; disodium hydrogenphosphate; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; camphor-10-sulfonic acid; dihydrogen peroxide; sodium hydride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; paraffin;

DOI:10.1021/jo980320p

Reference yield:

(2R,3S,6R)-6-allyl-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol (95791-07-4) → Trifluoro-methanesulfonic acid (2R,3S,4S,6R)-4-benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester (189347-96-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.46 g / m-CPBA, Na₂HPO₄ / toluene / 2 h / 0 °C

2: 1.13 g / CSA / CH₂Cl₂ / 48 h / Ambient temperature

3: 95 percent / LiAlH₄ / diethyl ether / 1.5 h / Ambient temperature

4: 95 percent / NaH / dimethylformamide; paraffin / 3 h / Ambient temperature

5: 1.) 9-BBN-H, 2.) 3M NaOH, 30percent H₂O₂ / 1.) THF, room temperature, 4 h, 2.) room temperature, 1 h

6: 92 percent / NaH / dimethylformamide; paraffin / 3 h / Ambient temperature

7: 92 percent / conc.HCl / tetrahydrofuran; H₂O / 5 h / 40 °C

8: 1.) 2,6-lutidine / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) -78 deg C, 30 min

With 2,6-dimethylpyridine; hydrogenchloride; sodium hydroxide; disodium hydrogenphosphate; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; camphor-10-sulfonic acid; dihydrogen peroxide; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; paraffin;

DOI:10.1021/jo980320p

upstream raw materials:

trifluoromethylsulfonic anhydride

triethylsilyl trifluoromethyl sulfonate

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

(2R,3S,6R)-2-acetoxymethyl-6-allyl-3,6-dihydro-2H-pyran-3-yl acetate

Downstream raw materials:

(2R,4S,4aS,5aR,8S,9R,10aS,11aR)-4-Benzyloxy-2-(3-benzyloxy-propyl)-9-[(2R,3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-2-(toluene-4-sulfonyl)-oxiranylmethyl]-5a-methyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol

C₅₄H₇₂O₈Si

C₆₅H₈₈O₁₀SSi₂

(S)-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranyl]-[(2R,3S,4aR,6R,8S,8aS)-8-benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-3-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol

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