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

Base Information

Chemical Name:(2R,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-10-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undecan-4-one
CAS No.:194342-89-7
Molecular Formula:C₃₃H₄₇BrO₇Si
Molecular Weight:663.721
Hs Code.:

Synonyms:(2R,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-10-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undecan-4-one

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Chemical Property of (2R,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-10-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undecan-4-one

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Technology Process of (2R,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-10-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undecan-4-one

There total 21 articles about (2R,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-10-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undecan-4-one 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:

: 80910-01-6,108836-41-5,144069-33-0,134733-19-0
(R)-2-(((4-methoxybenzyl)oxy)methyl)oxirane

: 194342-89-7
(2R,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-10-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undecan-4-one

Guidance literature:: Multi-step reaction with 8 steps

1: 85 percent / CuI / tetrahydrofuran / 2 h / -78 - 0 °C

2: 98 percent / PPTS / CH₂Cl₂ / 5 h / Ambient temperature

3: 1.) OsO₄, NMO; 2.) NaIO₄ / 1.) aq. THF, r.t., 1.75 h; 2.) aq. THF, r.t., 1 h

4: 89 percent / 1.) (-)-Ipc₂BCl, Et₃N / diethyl ether / 1.) 0 deg C, 2 h; 2.) -78 deg C, 4 h then -20 deg C, 16 h

5: 95 percent / pyridine / benzene / 4 h / Ambient temperature

6: 60 percent / BF₃*OEt₂, PhSH / CH₂Cl₂ / 2 h / -20 - 0 °C

7: 95 percent / imid / dimethylformamide / 6 h / Ambient temperature

8: 1.) Dibal-H; 2.) (n-Pr)4NRuO₄, NMO, 4A MS / 1.) CH₂Cl₂, -78 deg C, 3 h; 2.) CH₂Cl₂, r.t., 2 h

With pyridine; 1H-imidazole; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; thiophenol; triethylamine; (-)-diisopinocamphenylborane chloride; copper(l) iodide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(97)01140-4

Reference yield:

: 18982-54-2
o-bromobenzyl alcohol

: 194342-89-7
(2R,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-10-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undecan-4-one

Guidance literature:: Multi-step reaction with 16 steps

1: 96 percent / NaH / tetrahydrofuran / 4 h / Ambient temperature

2: 1.) 9-BBN; 2.) NaOH, H₂O₂ / 1.) THF, irrad., r.t., 3 h; 2.) reflux, 1 h

3: 76 percent / PCC, Celite / CH₂Cl₂ / 4 h / Ambient temperature

4: 83 percent / 1.) Sn(OTf)2, N-ethylpiperidine / CH₂Cl₂ / 1.) -50 deg C to -40 deg C, 4 h; 2.) -78 deg C, 4 h

5: 94 percent / Me₃Al / toluene; CH₂Cl₂ / -25 - 0 °C

6: 97 percent / PPTS / CH₂Cl₂ / 18 h / Ambient temperature

7: 96 percent / Dibal-H / tetrahydrofuran; hexane / 2 h / -78 °C

8: 68 percent / 1.) Sn(OTf)2, N-ethylpiperidine / CH₂Cl₂ / 1.) -50 deg C to -40 deg C, 4 h; 2.) -78 deg C, 4 h

9: 88 percent / Me₃Al / toluene; CH₂Cl₂ / -25 - 0 °C

10: 99 percent / imid / dimethylformamide / 6 h / Ambient temperature

11: tetrahydrofuran; diethyl ether / 2 h / -78 - 0 °C

12: 89 percent / 1.) (-)-Ipc₂BCl, Et₃N / diethyl ether / 1.) 0 deg C, 2 h; 2.) -78 deg C, 4 h then -20 deg C, 16 h

13: 95 percent / pyridine / benzene / 4 h / Ambient temperature

14: 60 percent / BF₃*OEt₂, PhSH / CH₂Cl₂ / 2 h / -20 - 0 °C

15: 95 percent / imid / dimethylformamide / 6 h / Ambient temperature

16: 1.) Dibal-H; 2.) (n-Pr)4NRuO₄, NMO, 4A MS / 1.) CH₂Cl₂, -78 deg C, 3 h; 2.) CH₂Cl₂, r.t., 2 h

With 1-ethyl-piperidine; pyridine; 1H-imidazole; sodium hydroxide; tin(II) trifluoromethanesulfonate; 9-borabicyclo[3.3.1]nonane dimer; N-methyl-2-indolinone; tetrapropylammonium perruthennate; Celite; boron trifluoride diethyl etherate; dihydrogen peroxide; trimethylaluminum; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; thiophenol; triethylamine; (-)-diisopinocamphenylborane chloride; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1016/S0040-4039(97)01140-4

Reference yield:

: 87280-01-1
1-((allyloxy)methyl)-2-bromobenzene

: 194342-89-7
(2R,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-10-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undecan-4-one

Guidance literature:: Multi-step reaction with 15 steps

1: 1.) 9-BBN; 2.) NaOH, H₂O₂ / 1.) THF, irrad., r.t., 3 h; 2.) reflux, 1 h

2: 76 percent / PCC, Celite / CH₂Cl₂ / 4 h / Ambient temperature

3: 83 percent / 1.) Sn(OTf)2, N-ethylpiperidine / CH₂Cl₂ / 1.) -50 deg C to -40 deg C, 4 h; 2.) -78 deg C, 4 h

4: 94 percent / Me₃Al / toluene; CH₂Cl₂ / -25 - 0 °C

5: 97 percent / PPTS / CH₂Cl₂ / 18 h / Ambient temperature

6: 96 percent / Dibal-H / tetrahydrofuran; hexane / 2 h / -78 °C

7: 68 percent / 1.) Sn(OTf)2, N-ethylpiperidine / CH₂Cl₂ / 1.) -50 deg C to -40 deg C, 4 h; 2.) -78 deg C, 4 h

8: 88 percent / Me₃Al / toluene; CH₂Cl₂ / -25 - 0 °C

9: 99 percent / imid / dimethylformamide / 6 h / Ambient temperature

10: tetrahydrofuran; diethyl ether / 2 h / -78 - 0 °C

11: 89 percent / 1.) (-)-Ipc₂BCl, Et₃N / diethyl ether / 1.) 0 deg C, 2 h; 2.) -78 deg C, 4 h then -20 deg C, 16 h

12: 95 percent / pyridine / benzene / 4 h / Ambient temperature

13: 60 percent / BF₃*OEt₂, PhSH / CH₂Cl₂ / 2 h / -20 - 0 °C

14: 95 percent / imid / dimethylformamide / 6 h / Ambient temperature

15: 1.) Dibal-H; 2.) (n-Pr)4NRuO₄, NMO, 4A MS / 1.) CH₂Cl₂, -78 deg C, 3 h; 2.) CH₂Cl₂, r.t., 2 h

With 1-ethyl-piperidine; pyridine; 1H-imidazole; sodium hydroxide; tin(II) trifluoromethanesulfonate; 9-borabicyclo[3.3.1]nonane dimer; N-methyl-2-indolinone; tetrapropylammonium perruthennate; Celite; boron trifluoride diethyl etherate; dihydrogen peroxide; trimethylaluminum; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; thiophenol; triethylamine; (-)-diisopinocamphenylborane chloride; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1016/S0040-4039(97)01140-4