Trifluoro-methanesulfonic acid (2R,3R,4R,4aS,9aS)-4-(4-bromo-benzyloxy)-3-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-ylmethyl ester

Base Information

• Chemical Name: Trifluoro-methanesulfonic acid (2R,3R,4R,4aS,9aS)-4-(4-bromo-benzyloxy)-3-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-ylmethyl ester
• CAS No.: 784157-69-3
• Molecular Formula: C₂₉H₂₈BrF₃O₇S
• Molecular Weight: 657.502
• Mol file: 784157-69-3.mol

Synonyms:Trifluoro-methanesulfonic acid (2R,3R,4R,4aS,9aS)-4-(4-bromo-benzyloxy)-3-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-ylmethyl ester

Chemical Property of Trifluoro-methanesulfonic acid (2R,3R,4R,4aS,9aS)-4-(4-bromo-benzyloxy)-3-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Trifluoro-methanesulfonic acid (2R,3R,4R,4aS,9aS)-4-(4-bromo-benzyloxy)-3-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-ylmethyl ester

There total 15 articles about Trifluoro-methanesulfonic acid (2R,3R,4R,4aS,9aS)-4-(4-bromo-benzyloxy)-3-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-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) + ((2R,3R,4R,4aS,9aS)-4-((4-bromobenzyl)oxy)-3-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-pyrano[3,2-b]oxepin-2-yl)methanol → Trifluoro-methanesulfonic acid (2R,3R,4R,4aS,9aS)-4-(4-bromo-benzyloxy)-3-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-ylmethyl ester (784157-69-3)

Guidance literature:

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

DOI:10.1016/j.tetlet.2004.07.145

Reference yield:

allyl 4,6-O-benzylidene-D-glucopyranoside (259882-15-0) → Trifluoro-methanesulfonic acid (2R,3R,4R,4aS,9aS)-4-(4-bromo-benzyloxy)-3-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-ylmethyl ester (784157-69-3)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 95 percent / imidazole / dimethylformamide / 23 °C

2.1: 99 percent / Et₃Al / [NiCl₂(dpp)] / toluene / 0 - 24 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

4.1: diethyl ether / -78 °C

5.1: 80 percent / BF₃*OEt₂ / CH₂Cl₂ / -20 °C

6.1: mCPBA / CH₂Cl₂ / 0 °C

6.2: 80 percent / Et₃SiH; BF₃*OEt₂ / 0 °C

7.1: 92 percent / PPTS / benzene / Heating

8.1: 90 percent / TBAF / tetrahydrofuran / 23 °C

9.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

10.1: NaH; Bu₄NI / tetrahydrofuran / 0 °C

11.1: (Cy₃P)2Cl₂Ru=CHPh / CH₂Cl₂ / Heating

12.1: TBAF / tetrahydrofuran / 23 °C

13.1: NaH; Bu₄NI / tetrahydrofuran / 24 °C

14.1: LiAlH₄; AlCl₃ / CH₂Cl₂; diethyl ether / 24 °C

15.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; lithium aluminium tetrahydride; aluminium trichloride; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; triethylaluminum; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; Grubbs catalyst first generation; [NiCl₂(dpp)]; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 3.1: Swern oxidation / 4.1: Grignard reaction;

DOI:10.1016/j.tetlet.2004.07.145

Reference yield:

4,6-O-benzylidene-2,3-O-(3,5-diisopropyl-2,6-dimethyl-4-oxa-3,5-disilaheptane-3,5-diyl)-D-glucopyranose → Trifluoro-methanesulfonic acid (2R,3R,4R,4aS,9aS)-4-(4-bromo-benzyloxy)-3-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-ylmethyl ester (784157-69-3)

Guidance literature:

Multi-step reaction with 13 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

2.1: diethyl ether / -78 °C

3.1: 80 percent / BF₃*OEt₂ / CH₂Cl₂ / -20 °C

4.1: mCPBA / CH₂Cl₂ / 0 °C

4.2: 80 percent / Et₃SiH; BF₃*OEt₂ / 0 °C

5.1: 92 percent / PPTS / benzene / Heating

6.1: 90 percent / TBAF / tetrahydrofuran / 23 °C

7.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

8.1: NaH; Bu₄NI / tetrahydrofuran / 0 °C

9.1: (Cy₃P)2Cl₂Ru=CHPh / CH₂Cl₂ / Heating

10.1: TBAF / tetrahydrofuran / 23 °C

11.1: NaH; Bu₄NI / tetrahydrofuran / 24 °C

12.1: LiAlH₄; AlCl₃ / CH₂Cl₂; diethyl ether / 24 °C

13.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; aluminium trichloride; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane; benzene; 1.1: Swern oxidation / 2.1: Grignard reaction;

DOI:10.1016/j.tetlet.2004.07.145

upstream raw materials:

trifluoromethylsulfonic anhydride

1-bromomethyl-4-bromobenzene

allyl 4,6-O-benzylidene-D-glucopyranoside

4,6-O-benzylidene-2,3-O-(3,5-diisopropyl-2,6-dimethyl-4-oxa-3,5-disilaheptane-3,5-diyl)-D-glucono-1,5-lactone

Downstream raw materials:

(2R,3R,4R,4aS,9aS)-4-((4-bromobenzyl)oxy)-2-(2-(methylsulfinyl)-2-(methylthio)ethyl)-3-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-pyrano[3,2-b]oxepine