(2R,4aR,5aS,10aS,11R,11aR)-11-(4-Bromo-benzyloxy)-2-naphthalen-2-yl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

Base Information

• Chemical Name: (2R,4aR,5aS,10aS,11R,11aR)-11-(4-Bromo-benzyloxy)-2-naphthalen-2-yl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene
• CAS No.: 784157-68-2
• Molecular Formula: C₂₈H₂₇BrO₅
• Molecular Weight: 523.423
• Mol file: 784157-68-2.mol

Synonyms:(2R,4aR,5aS,10aS,11R,11aR)-11-(4-Bromo-benzyloxy)-2-naphthalen-2-yl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

Chemical Property of (2R,4aR,5aS,10aS,11R,11aR)-11-(4-Bromo-benzyloxy)-2-naphthalen-2-yl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4aR,5aS,10aS,11R,11aR)-11-(4-Bromo-benzyloxy)-2-naphthalen-2-yl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

There total 11 articles about (2R,4aR,5aS,10aS,11R,11aR)-11-(4-Bromo-benzyloxy)-2-naphthalen-2-yl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene 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:

1-bromomethyl-4-bromobenzene (589-15-1) + (2R,4aR,5aS,10aR,11R,11aS)-2-(naphthalen-2-yl)-4,4a,5a,6,9,10a,11,11a-octahydro-[1,3]dioxino[40,50:5,6]pyrano[3,2-b]oxepin-11-ol (784157-67-1) → (2R,4aR,5aS,10aS,11R,11aR)-11-(4-Bromo-benzyloxy)-2-naphthalen-2-yl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene (784157-68-2)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 24 ℃;

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 → (2R,4aR,5aS,10aS,11R,11aR)-11-(4-Bromo-benzyloxy)-2-naphthalen-2-yl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene (784157-68-2)

Guidance literature:

Multi-step reaction with 11 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

With 2,6-dimethylpyridine; 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

Reference yield:

(5aS,5bR,7R,9aR,11aR)-11-(allyloxy)-2,2,4,4-tetraisopropyl-7-phenylhexahydro[1,3]dioxino[4',5':5,6]pyrano[3,4-f] [1,3,5,2,4]trioxadisilepine (784157-61-5) → (2R,4aR,5aS,10aS,11R,11aR)-11-(4-Bromo-benzyloxy)-2-naphthalen-2-yl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene (784157-68-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 99 percent / Et₃Al / [NiCl₂(dpp)] / toluene / 0 - 24 °C

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

3.1: diethyl ether / -78 °C

4.1: 80 percent / BF₃*OEt₂ / CH₂Cl₂ / -20 °C

5.1: mCPBA / CH₂Cl₂ / 0 °C

5.2: 80 percent / Et₃SiH; BF₃*OEt₂ / 0 °C

6.1: 92 percent / PPTS / benzene / Heating

7.1: 90 percent / TBAF / tetrahydrofuran / 23 °C

8.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

9.1: NaH; Bu₄NI / tetrahydrofuran / 0 °C

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

11.1: TBAF / tetrahydrofuran / 23 °C

12.1: NaH; Bu₄NI / tetrahydrofuran / 24 °C

With 2,6-dimethylpyridine; 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; toluene; benzene; 2.1: Swern oxidation / 3.1: Grignard reaction;

DOI:10.1016/j.tetlet.2004.07.145

upstream raw materials:

1-bromomethyl-4-bromobenzene

(2R,4aR,5aS,10aR,11R,11aS)-2-(naphthalen-2-yl)-4,4a,5a,6,9,10a,11,11a-octahydro-[1,3]dioxino[40,50:5,6]pyrano[3,2-b]oxepin-11-ol

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

(5aS,5bR,7R,9aR,11aR)-11-(allyloxy)-2,2,4,4-tetraisopropyl-7-phenylhexahydro[1,3]dioxino[4',5':5,6]pyrano[3,4-f] [1,3,5,2,4]trioxadisilepine

Downstream raw materials:

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

(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