Trifluoro-methanesulfonic acid (2S,3R,6S,7R)-6-benzyloxy-7-((R)-3-benzyloxy-1-methyl-propyl)-3-methyl-3-trimethylsilanyloxy-oxepan-2-ylmethyl ester

Base Information

• Chemical Name: Trifluoro-methanesulfonic acid (2S,3R,6S,7R)-6-benzyloxy-7-((R)-3-benzyloxy-1-methyl-propyl)-3-methyl-3-trimethylsilanyloxy-oxepan-2-ylmethyl ester
• CAS No.: 312487-67-5
• Molecular Formula: C₃₀H₄₃F₃O₇SSi
• Molecular Weight: 632.814

Synonyms:

Chemical Property of Trifluoro-methanesulfonic acid (2S,3R,6S,7R)-6-benzyloxy-7-((R)-3-benzyloxy-1-methyl-propyl)-3-methyl-3-trimethylsilanyloxy-oxepan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of Trifluoro-methanesulfonic acid (2S,3R,6S,7R)-6-benzyloxy-7-((R)-3-benzyloxy-1-methyl-propyl)-3-methyl-3-trimethylsilanyloxy-oxepan-2-ylmethyl ester

There total 19 articles about Trifluoro-methanesulfonic acid (2S,3R,6S,7R)-6-benzyloxy-7-((R)-3-benzyloxy-1-methyl-propyl)-3-methyl-3-trimethylsilanyloxy-oxepan-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:

(2R,3S,6S)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-hydroxymethyl-6-methyl-tetrahydro-pyran-3-ol (174198-73-3) → Trifluoro-methanesulfonic acid (2S,3R,6S,7R)-6-benzyloxy-7-((R)-3-benzyloxy-1-methyl-propyl)-3-methyl-3-trimethylsilanyloxy-oxepan-2-ylmethyl ester (312487-67-5)

Guidance literature:

Multi-step reaction with 19 steps

1: 2,4,6-collidine / CH₂Cl₂ / -78 °C

2: imidazole / dimethylformamide / 25 °C

3: K₂CO₃ / methanol / 25 °C

4: TPAP; NMO; MS-4 Angstroem / CH₂Cl₂ / 25 °C

5: LDA / tetrahydrofuran / -78 °C

6: TBAF / tetrahydrofuran / 25 °C

7: LiOH / H₂O; tetrahydrofuran / 0 °C

8: pyridine / 25 °C

9: 88 percent / DBU / benzene / 25 °C

10: 89 percent / diethyl ether / 0 °C

11: LiAlH₄ / diethyl ether / 0 - 25 °C

12: n-Bu₄NI; NaH / tetrahydrofuran / 0 - 25 °C

13: CSA / methanol / 25 °C

14: 2,4,6-collidine / CH₂Cl₂ / -78 °C

15: 2,6-lutidine / CH₂Cl₂ / 0 °C

16: Zn(AcO)2 / triethylamine; acetic acid; 2,2,4-trimethyl-pentane / reflux

17: K₂CO₃ / methanol / 25 °C

18: 2,6-lutidine / CH₂Cl₂ / -78 °C

19: 2,6-lutidine / CH₂Cl₂ / -78 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; lithium hydroxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; MS-4 Angstroem; zinc diacetate; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; camphor-10-sulfonic acid; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; dichloromethane; water; acetic acid; triethylamine; N,N-dimethyl-formamide; benzene; 1: Acetylation / 2: silylation / 3: Hydrolysis / 4: Oxidation / 5: Addition / 6: ether cleavage / 7: Hydrolysis / 8: Cyclization / 9: Elimination / 10: Addition / 11: Reduction / 12: Alkylation / 13: Hydrolysis / 14: Acetylation / 15: Acylation / 16: ring-expansion / 17: Hydrolysis / 18: Acylation / 19: silylation;

DOI:10.1016/S0040-4039(00)01340-X

Reference yield:

(4aR,6S,8aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-methyl-6,7,8,8a-tetrahydro-4aH-pyrano[3,2-b]pyran-2-one (312487-61-9) → Trifluoro-methanesulfonic acid (2S,3R,6S,7R)-6-benzyloxy-7-((R)-3-benzyloxy-1-methyl-propyl)-3-methyl-3-trimethylsilanyloxy-oxepan-2-ylmethyl ester (312487-67-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 89 percent / diethyl ether / 0 °C

2: LiAlH₄ / diethyl ether / 0 - 25 °C

3: n-Bu₄NI; NaH / tetrahydrofuran / 0 - 25 °C

4: CSA / methanol / 25 °C

5: 2,4,6-collidine / CH₂Cl₂ / -78 °C

6: 2,6-lutidine / CH₂Cl₂ / 0 °C

7: Zn(AcO)2 / triethylamine; acetic acid; 2,2,4-trimethyl-pentane / reflux

8: K₂CO₃ / methanol / 25 °C

9: 2,6-lutidine / CH₂Cl₂ / -78 °C

10: 2,6-lutidine / CH₂Cl₂ / -78 °C

With 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; lithium aluminium tetrahydride; zinc diacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; camphor-10-sulfonic acid; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; dichloromethane; acetic acid; triethylamine; 1: Addition / 2: Reduction / 3: Alkylation / 4: Hydrolysis / 5: Acetylation / 6: Acylation / 7: ring-expansion / 8: Hydrolysis / 9: Acylation / 10: silylation;

DOI:10.1016/S0040-4039(00)01340-X

Reference yield:

Acetic acid (2R,3S,6S)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-6-methyl-tetrahydro-pyran-2-ylmethyl ester → Trifluoro-methanesulfonic acid (2S,3R,6S,7R)-6-benzyloxy-7-((R)-3-benzyloxy-1-methyl-propyl)-3-methyl-3-trimethylsilanyloxy-oxepan-2-ylmethyl ester (312487-67-5)

Guidance literature:

Multi-step reaction with 18 steps

1: imidazole / dimethylformamide / 25 °C

2: K₂CO₃ / methanol / 25 °C

3: TPAP; NMO; MS-4 Angstroem / CH₂Cl₂ / 25 °C

4: LDA / tetrahydrofuran / -78 °C

5: TBAF / tetrahydrofuran / 25 °C

6: LiOH / H₂O; tetrahydrofuran / 0 °C

7: pyridine / 25 °C

8: 88 percent / DBU / benzene / 25 °C

9: 89 percent / diethyl ether / 0 °C

10: LiAlH₄ / diethyl ether / 0 - 25 °C

11: n-Bu₄NI; NaH / tetrahydrofuran / 0 - 25 °C

12: CSA / methanol / 25 °C

13: 2,4,6-collidine / CH₂Cl₂ / -78 °C

14: 2,6-lutidine / CH₂Cl₂ / 0 °C

15: Zn(AcO)2 / triethylamine; acetic acid; 2,2,4-trimethyl-pentane / reflux

16: K₂CO₃ / methanol / 25 °C

17: 2,6-lutidine / CH₂Cl₂ / -78 °C

18: 2,6-lutidine / CH₂Cl₂ / -78 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; lithium hydroxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; MS-4 Angstroem; zinc diacetate; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; camphor-10-sulfonic acid; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; dichloromethane; water; acetic acid; triethylamine; N,N-dimethyl-formamide; benzene; 1: silylation / 2: Hydrolysis / 3: Oxidation / 4: Addition / 5: ether cleavage / 6: Hydrolysis / 7: Cyclization / 8: Elimination / 9: Addition / 10: Reduction / 11: Alkylation / 12: Hydrolysis / 13: Acetylation / 14: Acylation / 15: ring-expansion / 16: Hydrolysis / 17: Acylation / 18: silylation;

DOI:10.1016/S0040-4039(00)01340-X

upstream raw materials:

trimethylsilyl trifluoromethanesulfonate

(2R,3S,6S)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-hydroxymethyl-6-methyl-tetrahydro-pyran-3-ol

(4aR,6S,8aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-methyl-6,7,8,8a-tetrahydro-4aH-pyrano[3,2-b]pyran-2-one

(4R,4aR,6S,8aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4,6-dimethyl-hexahydro-pyrano[3,2-b]pyran-2-one

Downstream raw materials:

{(2R,3R)-3-[(2S,3R,4aS,6R,7S,9aR)-7-Benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,9a-dimethyl-octahydro-1,5-dioxa-benzocyclohepten-2-ylmethyl]-2-methyl-oxiranyl}-methanol

2-[(2S,3R,4aS,6R,7S,9aR)-7-Benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,9a-dimethyl-octahydro-1,5-dioxa-benzocyclohepten-2-yl]-ethanol

{(2S,3R,6S,7R)-6-Benzyloxy-7-((R)-3-benzyloxy-1-methyl-propyl)-3-methyl-2-[(2R,3R)-3-methyl-3-((E)-styryl)-oxiranylmethyl]-oxepan-3-yloxy}-trimethyl-silane

(2S,3R,4aS,6R,7S,9aR)-7-Benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-2-((2R,3R)-3-hydroxymethyl-3-methyl-oxiranylmethyl)-2,9a-dimethyl-octahydro-1,5-dioxa-benzocyclohepten-3-ol

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