methyl (4R,5R,7S,2Z)-9-benzyloxy-7-hydroxy-5-(triisopropylsilyl)oxy-4-methylnon-2-enoate

Base Information

Chemical Name:methyl (4R,5R,7S,2Z)-9-benzyloxy-7-hydroxy-5-(triisopropylsilyl)oxy-4-methylnon-2-enoate
CAS No.:221627-45-8
Molecular Formula:C₂₇H₄₆O₅Si
Molecular Weight:478.745
Hs Code.:

Synonyms:methyl (4R,5R,7S,2Z)-9-benzyloxy-7-hydroxy-5-(triisopropylsilyl)oxy-4-methylnon-2-enoate

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Chemical Property of methyl (4R,5R,7S,2Z)-9-benzyloxy-7-hydroxy-5-(triisopropylsilyl)oxy-4-methylnon-2-enoate

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Technology Process of methyl (4R,5R,7S,2Z)-9-benzyloxy-7-hydroxy-5-(triisopropylsilyl)oxy-4-methylnon-2-enoate

There total 11 articles about methyl (4R,5R,7S,2Z)-9-benzyloxy-7-hydroxy-5-(triisopropylsilyl)oxy-4-methylnon-2-enoate 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: 86.0%

: 861118-73-2
methyl (4R,5R,7S,2Z)-9-benzyloxy-7-(tert-butyldimethylsilyl)oxy-5-(triisopropylsilyl)oxy-4-methylnon-2-enoate

: 221627-45-8
methyl (4R,5R,7S,2Z)-9-benzyloxy-7-hydroxy-5-(triisopropylsilyl)oxy-4-methylnon-2-enoate

Guidance literature:: With pyridinium p-toluenesulfonate; In methanol; at 55 ℃;
DOI:10.1016/S0040-4039(98)02693-8

Reference yield:

: 106064-33-9
isobutyl 5-(benzyloxy)-3-oxopentanoate

: 221627-45-8
methyl (4R,5R,7S,2Z)-9-benzyloxy-7-hydroxy-5-(triisopropylsilyl)oxy-4-methylnon-2-enoate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 99 percent / H₂ / Ru₂Cl₄[(S)-BIMAP]Et₃N / methanol / 60 h / 2585.74 Torr

2.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / -78 °C

3.1: 100 percent / DIBAL-H / toluene / 2 h / -78 °C

4.1: di-n-butylboron triflate; Et₃N / CH₂Cl₂ / -78 - 0 °C

5.1: 74 percent / Me₃Al / tetrahydrofuran; hexane / 3 h / 0 - 25 °C

6.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / -78 - 0 °C

7.1: 96 percent / diisobutylaluminum hydride / tetrahydrofuran / 1 h / -78 °C

8.1: 18-crown-6; potassium hexamethyldisilazide / tetrahydrofuran; toluene / 15 h / -78 °C

8.2: 94 percent / tetrahydrofuran; toluene / 3 h / -78 °C

9.1: 86 percent / PPTS / methanol / 18 h / 55 °C

With 2,6-dimethylpyridine; 18-crown-6 ether; di-n-butylboryl trifluoromethanesulfonate; hydrogen; trimethylaluminum; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; triethylamine; Ru₂Cl₄-(S)-(2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)2*NEt₃; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 4.1: Evans aldol coupling;
DOI:10.1021/jo0503862

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 221627-45-8
methyl (4R,5R,7S,2Z)-9-benzyloxy-7-hydroxy-5-(triisopropylsilyl)oxy-4-methylnon-2-enoate

Guidance literature:: Multi-step reaction with 10 steps

1.1: NaH / tetrahydrofuran / 0.75 h / 0 °C

1.2: n-BuLi / tetrahydrofuran; hexane / 0.75 h / -25 °C

1.3: 56 percent / tetrahydrofuran; hexane / 1 h / -25 °C

2.1: 99 percent / H₂ / Ru₂Cl₄[(S)-BIMAP]Et₃N / methanol / 60 h / 2585.74 Torr

3.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / -78 °C

4.1: 100 percent / DIBAL-H / toluene / 2 h / -78 °C

5.1: di-n-butylboron triflate; Et₃N / CH₂Cl₂ / -78 - 0 °C

6.1: 74 percent / Me₃Al / tetrahydrofuran; hexane / 3 h / 0 - 25 °C

7.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / -78 - 0 °C

8.1: 96 percent / diisobutylaluminum hydride / tetrahydrofuran / 1 h / -78 °C

9.1: 18-crown-6; potassium hexamethyldisilazide / tetrahydrofuran; toluene / 15 h / -78 °C

9.2: 94 percent / tetrahydrofuran; toluene / 3 h / -78 °C

10.1: 86 percent / PPTS / methanol / 18 h / 55 °C

With 2,6-dimethylpyridine; 18-crown-6 ether; di-n-butylboryl trifluoromethanesulfonate; hydrogen; trimethylaluminum; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; triethylamine; Ru₂Cl₄-(S)-(2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)2*NEt₃; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 5.1: Evans aldol coupling;
DOI:10.1021/jo0503862