(1R,3S,5S)-ethyl 5-<(tert-butyldimethylsilyl)oxy>-3-hydroxy-3-hydroxymethyl-2,2-dimethyl-6-methylenecyclohexanecarboxylate

Base Information

Chemical Name:(1R,3S,5S)-ethyl 5-<(tert-butyldimethylsilyl)oxy>-3-hydroxy-3-hydroxymethyl-2,2-dimethyl-6-methylenecyclohexanecarboxylate
CAS No.:147512-96-7
Molecular Formula:C₁₉H₃₆O₅Si
Molecular Weight:372.577
Hs Code.:

Synonyms:(1R,3S,5S)-ethyl 5-<(tert-butyldimethylsilyl)oxy>-3-hydroxy-3-hydroxymethyl-2,2-dimethyl-6-methylenecyclohexanecarboxylate

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Chemical Property of (1R,3S,5S)-ethyl 5-<(tert-butyldimethylsilyl)oxy>-3-hydroxy-3-hydroxymethyl-2,2-dimethyl-6-methylenecyclohexanecarboxylate

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Technology Process of (1R,3S,5S)-ethyl 5-<(tert-butyldimethylsilyl)oxy>-3-hydroxy-3-hydroxymethyl-2,2-dimethyl-6-methylenecyclohexanecarboxylate

There total 13 articles about (1R,3S,5S)-ethyl 5-<(tert-butyldimethylsilyl)oxy>-3-hydroxy-3-hydroxymethyl-2,2-dimethyl-6-methylenecyclohexanecarboxylate 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: 80.0%

: 113355-14-9
(4S,6R)-(2Z)-ethyl 4-<(tert-butyldimethylsilyl)oxy>-6,7-epoxy-6-hydroxymethyl-7-methyl-3-<(trimethylsilyl)methyl>-2-octenoate

: 113308-85-3,147512-96-7
(3S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-3-hydroxymethyl-2,2-dimethyl-6-methylene-cyclohexanecarboxylic acid ethyl ester

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 0.25h;
DOI:10.1016/S0040-4039(00)96200-2

Reference yield:

: (7S,8S)-8-(tert-Butyl-dimethyl-silanyloxy)-3,3-dimethyl-1,6-dioxa-spiro[3.5]nonane-2,7-diol

: 113308-85-3,147512-96-7
(3S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-3-hydroxymethyl-2,2-dimethyl-6-methylene-cyclohexanecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: PDC, Ac₂O / CH₂Cl₂

2: 170 °C

3: 79 percent

4: pyridinium tosylate

5: 1.) (TMS)2NLi / 1.) TMEDA

6: 83 percent / KOtBu

7: 5 percent Ni(acac)2

8: pyridinium tosylate / propan-2-ol / 50 °C

9: Ti(OiPr)4, (-)-DET, TBHP / -25 °C

10: 80 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.25 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dipyridinium dichromate; boron trifluoride diethyl etherate; potassium tert-butylate; pyridinium p-toluenesulfonate; acetic anhydride; (-)-diethyl tartrate; lithium hexamethyldisilazane; bis(acetylacetonate)nickel(II); In dichloromethane; isopropyl alcohol;
DOI:10.1016/S0040-4039(00)96200-2

Reference yield:

: 113308-81-9
(2S)-2-<(tert-butyldimethylsilyl)oxy>-4-hydroxymethyl-5-methyl-4-hexanoic acid ?-lactone

: 113308-85-3,147512-96-7
(3S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-3-hydroxymethyl-2,2-dimethyl-6-methylene-cyclohexanecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 79 percent

2: pyridinium tosylate

3: 1.) (TMS)2NLi / 1.) TMEDA

4: 83 percent / KOtBu

5: 5 percent Ni(acac)2

6: pyridinium tosylate / propan-2-ol / 50 °C

7: Ti(OiPr)4, (-)-DET, TBHP / -25 °C

8: 80 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.25 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; boron trifluoride diethyl etherate; potassium tert-butylate; pyridinium p-toluenesulfonate; (-)-diethyl tartrate; lithium hexamethyldisilazane; bis(acetylacetonate)nickel(II); In dichloromethane; isopropyl alcohol;
DOI:10.1016/S0040-4039(00)96200-2