[(2S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(2-nitro-phenylselanylmethyl)-cyclohex-(Z)-ylidene]-acetic acid methyl ester

Base Information

• Chemical Name: [(2S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(2-nitro-phenylselanylmethyl)-cyclohex-(Z)-ylidene]-acetic acid methyl ester
• CAS No.: 129482-79-7
• Molecular Formula: C₂₈H₄₇NO₆SeSi₂
• Molecular Weight: 628.815

Synonyms:[(2S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(2-nitro-phenylselanylmethyl)-cyclohex-(Z)-ylidene]-acetic acid methyl ester

Chemical Property of [(2S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(2-nitro-phenylselanylmethyl)-cyclohex-(Z)-ylidene]-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(2-nitro-phenylselanylmethyl)-cyclohex-(Z)-ylidene]-acetic acid methyl ester

There total 19 articles about [(2S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(2-nitro-phenylselanylmethyl)-cyclohex-(Z)-ylidene]-acetic acid methyl 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: 84.0%

ortho-nitrophenyl selenocyanate (51694-22-5) + [(2R,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclohex-(Z)-ylidene]-acetic acid methyl ester (129482-78-6) → [(2S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(2-nitro-phenylselanylmethyl)-cyclohex-(Z)-ylidene]-acetic acid methyl ester (129482-79-7)

Guidance literature:

With tributylphosphine; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/0040-4039(90)80021-D

Reference yield:

(3aR,7aS)-1,3,3a,4,7,7a-hexahydroisobenzofuran-1-one (65376-03-6) → [(2S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(2-nitro-phenylselanylmethyl)-cyclohex-(Z)-ylidene]-acetic acid methyl ester (129482-79-7)

Guidance literature:

Multi-step reaction with 16 steps

1: aq. NaOH / tetrahydrofuran / Ambient temperature

2: I₂, KI / H₂O; CH₂Cl₂ / Ambient temperature

3: imidazole / dimethylformamide / Ambient temperature

4: 99 percent / DBU / toluene / Heating

5: 89 percent / MCPBA

6: DIBAL / toluene / -78 °C

8: LiAlH₄ / tetrahydrofuran / Ambient temperature; or Red-Al

9: p-TsOH / tetrahydrofuran

10: 86 percent / imidazole / dimethylformamide / Ambient temperature

11: 81 percent / NBS / acetone; H₂O / -15 °C

12: LDA / tetrahydrofuran / -78 °C

13: H₂O₂ / tetrahydrofuran / 0 deg C -> room temperature

14: aq. NaOH / methanol / Ambient temperature

15: diethyl ether / 0 °C

16: 84 percent / n-Bu₃P / tetrahydrofuran / Ambient temperature

With 1H-imidazole; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; tributylphosphine; dihydrogen peroxide; iodine; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; potassium iodide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1016/0040-4039(90)80021-D

Reference yield:

(1S,6R)-Methyl 6-Hydroxymethyl-3-cyclohexene-1-carboxylate (104265-90-9) → [(2S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(2-nitro-phenylselanylmethyl)-cyclohex-(Z)-ylidene]-acetic acid methyl ester (129482-79-7)

Guidance literature:

Multi-step reaction with 17 steps

1: p-TsOH / benzene / Ambient temperature

2: aq. NaOH / tetrahydrofuran / Ambient temperature

3: I₂, KI / H₂O; CH₂Cl₂ / Ambient temperature

4: imidazole / dimethylformamide / Ambient temperature

5: 99 percent / DBU / toluene / Heating

6: 89 percent / MCPBA

7: DIBAL / toluene / -78 °C

9: LiAlH₄ / tetrahydrofuran / Ambient temperature; or Red-Al

10: p-TsOH / tetrahydrofuran

11: 86 percent / imidazole / dimethylformamide / Ambient temperature

12: 81 percent / NBS / acetone; H₂O / -15 °C

13: LDA / tetrahydrofuran / -78 °C

14: H₂O₂ / tetrahydrofuran / 0 deg C -> room temperature

15: aq. NaOH / methanol / Ambient temperature

16: diethyl ether / 0 °C

17: 84 percent / n-Bu₃P / tetrahydrofuran / Ambient temperature

With 1H-imidazole; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; tributylphosphine; dihydrogen peroxide; iodine; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; potassium iodide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; benzene;

DOI:10.1016/0040-4039(90)80021-D

upstream raw materials:

ortho-nitrophenyl selenocyanate

[(2R,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclohex-(Z)-ylidene]-acetic acid methyl ester

(3aR,7aS)-1,3,3a,4,7,7a-hexahydroisobenzofuran-1-one

(1S,6R)-Methyl 6-Hydroxymethyl-3-cyclohexene-1-carboxylate

Downstream raw materials:

methyl (Z,3S,5R)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]acetate

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