(4S,6S)-8-(2-Bromo-benzyloxy)-4-(tert-butyl-dimethyl-silanyloxy)-6-(tetrahydro-pyran-2-yloxy)-octan-2-one

Base Information

• Chemical Name: (4S,6S)-8-(2-Bromo-benzyloxy)-4-(tert-butyl-dimethyl-silanyloxy)-6-(tetrahydro-pyran-2-yloxy)-octan-2-one
• CAS No.: 194342-75-1
• Molecular Formula: C₂₆H₄₃BrO₅Si
• Molecular Weight: 543.614

Synonyms:(4S,6S)-8-(2-Bromo-benzyloxy)-4-(tert-butyl-dimethyl-silanyloxy)-6-(tetrahydro-pyran-2-yloxy)-octan-2-one

Chemical Property of (4S,6S)-8-(2-Bromo-benzyloxy)-4-(tert-butyl-dimethyl-silanyloxy)-6-(tetrahydro-pyran-2-yloxy)-octan-2-one

Chemical Property:

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Technology Process of (4S,6S)-8-(2-Bromo-benzyloxy)-4-(tert-butyl-dimethyl-silanyloxy)-6-(tetrahydro-pyran-2-yloxy)-octan-2-one

There total 12 articles about (4S,6S)-8-(2-Bromo-benzyloxy)-4-(tert-butyl-dimethyl-silanyloxy)-6-(tetrahydro-pyran-2-yloxy)-octan-2-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: 92.0%

methylmagnesium bromide (75-16-1) + (3S,5S)-7-(2-Bromo-benzyloxy)-3-(tert-butyl-dimethyl-silanyloxy)-5-(tetrahydro-pyran-2-yloxy)-heptanoic acid methoxy-methyl-amide → (4S,6S)-8-(2-Bromo-benzyloxy)-4-(tert-butyl-dimethyl-silanyloxy)-6-(tetrahydro-pyran-2-yloxy)-octan-2-one (194342-75-1)

Guidance literature:

In tetrahydrofuran; diethyl ether; at -78 - 0 ℃;

DOI:10.1135/cccc2008181

Reference yield:

o-bromobenzyl alcohol (18982-54-2) → (4S,6S)-8-(2-Bromo-benzyloxy)-4-(tert-butyl-dimethyl-silanyloxy)-6-(tetrahydro-pyran-2-yloxy)-octan-2-one (194342-75-1)

Guidance literature:

Multi-step reaction with 11 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

With 1-ethyl-piperidine; 1H-imidazole; sodium hydroxide; tin(II) trifluoromethanesulfonate; 9-borabicyclo[3.3.1]nonane dimer; Celite; dihydrogen peroxide; trimethylaluminum; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(97)01140-4

Reference yield:

1-((allyloxy)methyl)-2-bromobenzene (87280-01-1) → (4S,6S)-8-(2-Bromo-benzyloxy)-4-(tert-butyl-dimethyl-silanyloxy)-6-(tetrahydro-pyran-2-yloxy)-octan-2-one (194342-75-1)

Guidance literature:

Multi-step reaction with 10 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

With 1-ethyl-piperidine; 1H-imidazole; sodium hydroxide; tin(II) trifluoromethanesulfonate; 9-borabicyclo[3.3.1]nonane dimer; Celite; dihydrogen peroxide; trimethylaluminum; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(97)01140-4

upstream raw materials:

methylmagnesium bromide

o-bromobenzyl alcohol

1-((allyloxy)methyl)-2-bromobenzene

3-((2-bromobenzyl)oxy)propan-1-ol

Downstream raw materials:

C₄₃H₆₇BrO₁₀Si

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

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

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

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