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

Base Information

• Chemical Name: methyl (Z,3S,5R)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]acetate
• CAS No.: 129482-80-0
• Molecular Formula: C₂₂H₄₂O₄Si₂
• Molecular Weight: 426.744

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

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

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

There total 41 articles about methyl (Z,3S,5R)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]acetate 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%

[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-acetic acid methyl ester → methyl (Z,3S,5R)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]acetate (129482-80-0)

Guidance literature:

With 9-fluorenone; In tetrahydrofuran; Irradiation;

DOI:10.1016/S0040-4039(97)01005-8

Reference yield: 90.0%

(5R,7S,2Z)-8-Bromo-5,7-bis<(tert-butyldimethylsilyl)oxy>-2,8-nonadienoic acid methyl ester (137892-15-0) → methyl (Z,3S,5R)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]acetate (129482-80-0)

Guidance literature:

With potassium carbonate; Pd(PPh₃)(OAc)2; In acetonitrile; Heating;

DOI:10.1016/S0040-4039(00)93501-9

Reference yield: 81.0%

[(2S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(2-nitro-phenylselanylmethyl)-cyclohex-(Z)-ylidene]-acetic acid methyl ester (129482-79-7) → methyl (Z,3S,5R)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]acetate (129482-80-0)

Guidance literature:

With dihydrogen peroxide; In tetrahydrofuran; 0 deg C -> room temperature;

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

upstream raw materials:

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

(5R,7S,2Z)-8-Bromo-5,7-bis<(tert-butyldimethylsilyl)oxy>-2,8-nonadienoic acid methyl ester

methanol

carbon monoxide

Downstream raw materials:

[3S-(1Z,3α,5β)]-2-[3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethanol

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