2-(2-{3-[8-benzyloxy-9-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-ylmethyl]-2-methyl-oxiranyl}-2-triethylsilanyloxy-ethyl)-7-(4-bromo-benzyloxy)-8-(4-bromo-benzyloxymethyl)-5-methyl-oxocan-3-ol

Base Information

• Chemical Name: 2-(2-{3-[8-benzyloxy-9-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-ylmethyl]-2-methyl-oxiranyl}-2-triethylsilanyloxy-ethyl)-7-(4-bromo-benzyloxy)-8-(4-bromo-benzyloxymethyl)-5-methyl-oxocan-3-ol
• CAS No.: 876288-66-3
• Molecular Formula: C₆₄H₉₂Br₂O₁₀Si₂
• Molecular Weight: 1237.41

Synonyms:2-(2-{3-[8-benzyloxy-9-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-ylmethyl]-2-methyl-oxiranyl}-2-triethylsilanyloxy-ethyl)-7-(4-bromo-benzyloxy)-8-(4-bromo-benzyloxymethyl)-5-methyl-oxocan-3-ol

Chemical Property of 2-(2-{3-[8-benzyloxy-9-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-ylmethyl]-2-methyl-oxiranyl}-2-triethylsilanyloxy-ethyl)-7-(4-bromo-benzyloxy)-8-(4-bromo-benzyloxymethyl)-5-methyl-oxocan-3-ol

Chemical Property:

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Technology Process of 2-(2-{3-[8-benzyloxy-9-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-ylmethyl]-2-methyl-oxiranyl}-2-triethylsilanyloxy-ethyl)-7-(4-bromo-benzyloxy)-8-(4-bromo-benzyloxymethyl)-5-methyl-oxocan-3-ol

There total 31 articles about 2-(2-{3-[8-benzyloxy-9-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-ylmethyl]-2-methyl-oxiranyl}-2-triethylsilanyloxy-ethyl)-7-(4-bromo-benzyloxy)-8-(4-bromo-benzyloxymethyl)-5-methyl-oxocan-3-ol 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: 97.0%

C72H100Br2O11Si2 (876288-86-7) → 2-(2-{3-[8-benzyloxy-9-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-ylmethyl]-2-methyl-oxiranyl}-2-triethylsilanyloxy-ethyl)-7-(4-bromo-benzyloxy)-8-(4-bromo-benzyloxymethyl)-5-methyl-oxocan-3-ol (876288-66-3)

Guidance literature:

With pH 7 buffer; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 0 ℃; for 0.833333h; pH=7;

DOI:10.1016/j.tet.2006.05.014

Reference yield:

(2R,3S,5Z,8R,9S)-8-benzyloxy-9-benzyloxymethyl-2-hydroxymethyl-2,3,4,7,8,9-hexahydrooxonin-3-ol (876288-77-6) → 2-(2-{3-[8-benzyloxy-9-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-ylmethyl]-2-methyl-oxiranyl}-2-triethylsilanyloxy-ethyl)-7-(4-bromo-benzyloxy)-8-(4-bromo-benzyloxymethyl)-5-methyl-oxocan-3-ol (876288-66-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0.25 h / -78 °C

2.1: 17.5 mg / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 - 0 °C

3.1: BuLi / tetrahydrofuran / 0.17 h / -78 °C

3.2: 99 percent / tetrahydrofuran / 3 h / -78 - 24 °C

4.1: Cp₂ZrCl₂; DIBAL / tetrahydrofuran; hexane / 0.5 h / 55 °C

4.2: 86 percent / I₂ / tetrahydrofuran; hexane / 0.25 h / 0 °C

5.1: 40 percent / CrCl₂; NiCl₂ / dimethylsulfoxide / 25 h / 25 °C

6.1: VO(acac)2; TBHP / toluene / 2.5 h / 0 °C

6.2: 91 percent / dimethylsulfide / toluene / 0.5 h / 24 °C

7.1: 100 percent / 2,6-lutidine / tetrahydrofuran / 0.17 h / 0 - 25 °C

8.1: 97 percent / DDQ; pH 7 buffer / CH₂Cl₂ / 0.83 h / 0 °C / pH 7

With 2,6-dimethylpyridine; chromium dichloride; tert.-butylhydroperoxide; n-butyllithium; zirconocene dichloride; bis(acetylacetonate)oxovanadium; pH 7 buffer; diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; toluene; 5.1: Nozaki-Hiyama-Kishi reaction;

DOI:10.1016/j.tet.2006.05.014

Reference yield:

(1R,3S,4R,6Z,9S,11S)-4-benzyloxy-3-benzyloxymethyl-11-phenyl-2,10,12-trioxabicyclo[7.4.0]tridecan-6-ene (876288-76-5) → 2-(2-{3-[8-benzyloxy-9-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-ylmethyl]-2-methyl-oxiranyl}-2-triethylsilanyloxy-ethyl)-7-(4-bromo-benzyloxy)-8-(4-bromo-benzyloxymethyl)-5-methyl-oxocan-3-ol (876288-66-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 98 percent / aq. HCl / tetrahydrofuran / 21 h / 25 °C

2.1: 2,6-lutidine / CH₂Cl₂ / 0.25 h / -78 °C

3.1: 17.5 mg / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 - 0 °C

4.1: BuLi / tetrahydrofuran / 0.17 h / -78 °C

4.2: 99 percent / tetrahydrofuran / 3 h / -78 - 24 °C

5.1: Cp₂ZrCl₂; DIBAL / tetrahydrofuran; hexane / 0.5 h / 55 °C

5.2: 86 percent / I₂ / tetrahydrofuran; hexane / 0.25 h / 0 °C

6.1: 40 percent / CrCl₂; NiCl₂ / dimethylsulfoxide / 25 h / 25 °C

7.1: VO(acac)2; TBHP / toluene / 2.5 h / 0 °C

7.2: 91 percent / dimethylsulfide / toluene / 0.5 h / 24 °C

8.1: 100 percent / 2,6-lutidine / tetrahydrofuran / 0.17 h / 0 - 25 °C

9.1: 97 percent / DDQ; pH 7 buffer / CH₂Cl₂ / 0.83 h / 0 °C / pH 7

With 2,6-dimethylpyridine; chromium dichloride; hydrogenchloride; tert.-butylhydroperoxide; n-butyllithium; zirconocene dichloride; bis(acetylacetonate)oxovanadium; pH 7 buffer; diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; toluene; 6.1: Nozaki-Hiyama-Kishi reaction;

DOI:10.1016/j.tet.2006.05.014

upstream raw materials:

C₇₂H₁₀₀Br₂O₁₁Si₂

(2R,3S,5Z,8R,9S)-8-benzyloxy-9-benzyloxymethyl-2-hydroxymethyl-2,3,4,7,8,9-hexahydrooxonin-3-ol

(1R,3S,4R,6Z,9S,11S)-4-benzyloxy-3-benzyloxymethyl-11-phenyl-2,10,12-trioxabicyclo[7.4.0]tridecan-6-ene

(2R,3S,5Z,8R,9S)-3-benzyloxy-2-benzyloxymethyl-8-(tret-butyldimethylsilyloxy)-9-(but-2'-ynyl)-2,3,4,7,8,9-hexahydrooxonin

Downstream raw materials:

C₆₄H₉₂Br₂O₁₀Si₂

2-[1-benzyloxy-2-(8-benzyloxy-9-benzyloxymethyl-3-hydroxy-2,3,4,7,8,9-hexahydro-oxonin-2-yl)-ethyl]-7-(4-bromo-benzyloxy)-6-(4-bromo-benzyloxymethyl)-2,9-dimethyl-octahydro-1,5-dioxa-benzocycloocten-3-one

2-[8-benzyloxy-9-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-1-[7-(4-bromo-benzyloxy)-6-(4-bromo-benzyloxymethyl)-3-hydroxy-2,9-dimethyl-decahydro-1,5-dioxa-benzocycloocten-2-yl]-ethanone

2-{2-[8-benzyloxy-9-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-1-hydroxy-ethyl}-7-(4-bromo-benzyloxy)-6-(4-bromo-benzyloxymethyl)-2,9-dimethyl-decahydro-1,5-dioxa-benzocycloocten-3-ol

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