Acetic acid (2R,4S,6R,8S,10S)-8-[2-(2-bromo-benzyloxy)-ethyl]-2-(4-methoxy-benzyloxymethyl)-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undec-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,4S,6R,8S,10S)-8-[2-(2-bromo-benzyloxy)-ethyl]-2-(4-methoxy-benzyloxymethyl)-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undec-4-yl ester
• CAS No.: 262614-82-4
• Molecular Formula: C₃₅H₅₁BrO₉Si
• Molecular Weight: 723.774
• Mol file: 262614-82-4.mol

Synonyms:Acetic acid (2R,4S,6R,8S,10S)-8-[2-(2-bromo-benzyloxy)-ethyl]-2-(4-methoxy-benzyloxymethyl)-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undec-4-yl ester

Chemical Property of Acetic acid (2R,4S,6R,8S,10S)-8-[2-(2-bromo-benzyloxy)-ethyl]-2-(4-methoxy-benzyloxymethyl)-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undec-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,4S,6R,8S,10S)-8-[2-(2-bromo-benzyloxy)-ethyl]-2-(4-methoxy-benzyloxymethyl)-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undec-4-yl ester

There total 1 articles about Acetic acid (2R,4S,6R,8S,10S)-8-[2-(2-bromo-benzyloxy)-ethyl]-2-(4-methoxy-benzyloxymethyl)-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undec-4-yl 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: 95.0%

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) + Acetic acid (2R,4S,6R,8S,10S)-8-[2-(2-bromo-benzyloxy)-ethyl]-10-hydroxy-2-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undec-4-yl ester (194342-86-4) → Acetic acid (2R,4S,6R,8S,10S)-8-[2-(2-bromo-benzyloxy)-ethyl]-2-(4-methoxy-benzyloxymethyl)-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undec-4-yl ester (262614-82-4)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1021/ol0000049

Reference yield:

Acetic acid (2R,4S,6R,8S,10S)-8-[2-(2-bromo-benzyloxy)-ethyl]-2-(4-methoxy-benzyloxymethyl)-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undec-4-yl ester (262614-82-4) → [(2R,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undec-2-yl]-acetaldehyde (1025954-24-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / Dibal-H / CH₂Cl₂ / 0.75 h / -78 °C

2: 96 percent / TPAP; NMO; 4 Angstroem MS / CH₂Cl₂ / 1 h / 20 °C

3: 93 percent / tetrahydrofuran; diethyl ether / 2.5 h / -78 - 0 °C

4: 93 percent / DIPEA / CH₂Cl₂ / -40 - 0 °C

5: 90 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 20 °C

6: 82 percent / I₂; PPh₃; imidazole / benzene / 1.5 h / 20 °C

7: 100 percent / dimethylformamide / 36 h / 65 °C

8: (i-Pr₂)AlH / CH₂Cl₂ / 0.33 h / -78 °C

With 1H-imidazole; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 Angstroem MS; water; iodine; diisobutylaluminium hydride; diisopropyl aluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Reduction / 2: Oxidation / 3: Addition / 4: Condensation / 5: Hydrolysis / 6: Substitution / 7: Substitution / 8: Reduction;

DOI:10.1021/ol0000049

Reference yield:

Acetic acid (2R,4S,6R,8S,10S)-8-[2-(2-bromo-benzyloxy)-ethyl]-2-(4-methoxy-benzyloxymethyl)-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undec-4-yl ester (262614-82-4) → [(2R,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undec-2-yl]-methanol (262614-99-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / Dibal-H / CH₂Cl₂ / 0.75 h / -78 °C

2: 96 percent / TPAP; NMO; 4 Angstroem MS / CH₂Cl₂ / 1 h / 20 °C

3: 93 percent / tetrahydrofuran; diethyl ether / 2.5 h / -78 - 0 °C

4: 93 percent / DIPEA / CH₂Cl₂ / -40 - 0 °C

5: 90 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 20 °C

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 Angstroem MS; water; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; 1: Reduction / 2: Oxidation / 3: Addition / 4: Condensation / 5: Hydrolysis;

DOI:10.1021/ol0000049

upstream raw materials:

(2-trimethylethylsilylethoxy)methyl chloride

Acetic acid (2R,4S,6R,8S,10S)-8-[2-(2-bromo-benzyloxy)-ethyl]-10-hydroxy-2-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undec-4-yl ester

Downstream raw materials:

[(2R,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undec-2-yl]-acetaldehyde

[(2R,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undec-2-yl]-methanol

(2R,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-2-(4-methoxy-benzyloxymethyl)-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undecan-4-one

[(2S,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undec-2-yl]-acetonitrile