(1R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enecarboxylic acid

Base Information

Chemical Name:(1R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enecarboxylic acid
CAS No.:756893-85-3
Molecular Formula:C₁₄H₂₆O₄Si
Molecular Weight:286.444
Hs Code.:

Synonyms:(1R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enecarboxylic acid

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Chemical Property of (1R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enecarboxylic acid

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Technology Process of (1R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enecarboxylic acid

There total 8 articles about (1R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enecarboxylic acid 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: 99.0%

: 852380-46-2
(1R,3R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-4-methylene-6-oxa-bicyclo[3.2.1]octan-7-one

: 756893-85-3
(1R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enecarboxylic acid

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; at 0 ℃; for 7h;
DOI:10.1021/ja046695b

Reference yield: 99.0%

: 852380-48-4
(1R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enecarboxylic acid methyl ester

: 756893-85-3
(1R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enecarboxylic acid

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; at 0 ℃; for 7h; under 760 Torr;
DOI:10.1021/ja050586v

Reference yield:

: 77-95-2
D-(-)-quinic acid

: 756893-85-3
(1R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enecarboxylic acid

Guidance literature:: Multi-step reaction with 8 steps

1: Amberlyst H⁺ resin; benzene / dimethylformamide / Heating

2: triethylamine; DMAP / dimethylformamide / 23 °C

3: pyridinium dichromate; Celite; molecular sieves 4 Angstroem / acetonitrile / 45 °C

4: t-BuOK / tetrahydrofuran / 65 °C

5: 74 percent / molecular sieves 4 Angstroem / 5.5 h / 23 °C

6: 98 percent / triethylamine; DMAP / CH₂Cl₂ / 0.17 h / 23 °C

7: 89 percent / Pd(P(t-Bu)3)2; N-methylmorpholine N-oxide; triethylsilane / tetrahydrofuran / 3.5 h / 70 °C

8: 99 percent / H₂ / Pd/C / methanol / 7 h / 0 °C / 760 Torr

With triethylsilane; dmap; dipyridinium dichromate; bis(tri-t-butylphosphine)palladium⁽⁰⁾; 4 A molecular sieve; Amberlyst H⁺ resin; Celite; potassium tert-butylate; hydrogen; 4-methylmorpholine N-oxide; triethylamine; benzene; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 4: Wittig olefination;
DOI:10.1021/ja050586v