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

Base Information

Chemical Name:[(2R,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclohex-(Z)-ylidene]-acetic acid methyl ester
CAS No.:129482-78-6
Molecular Formula:C₂₂H₄₄O₅Si₂
Molecular Weight:444.759
Hs Code.:

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

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

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

There total 18 articles about [(2R,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-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:

: 65376-03-6
(3aR,7aS)-1,3,3a,4,7,7a-hexahydroisobenzofuran-1-one

: 129482-78-6
[(2R,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclohex-(Z)-ylidene]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 15 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

With 1H-imidazole; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; 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:

: 104265-90-9
(1S,6R)-Methyl 6-Hydroxymethyl-3-cyclohexene-1-carboxylate

: 129482-78-6
[(2R,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclohex-(Z)-ylidene]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 16 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

With 1H-imidazole; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; 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

Reference yield:

: 130695-72-6
(1S,2R,4R,5R)-2-Hydroxymethyl-4-iodo-6-oxabicyclo<3.2.1>octan-7-one

: 129482-78-6
[(2R,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclohex-(Z)-ylidene]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: imidazole / dimethylformamide / Ambient temperature

2: 99 percent / DBU / toluene / Heating

3: 89 percent / MCPBA

4: DIBAL / toluene / -78 °C

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

7: p-TsOH / tetrahydrofuran

8: 86 percent / imidazole / dimethylformamide / Ambient temperature

9: 81 percent / NBS / acetone; H₂O / -15 °C

10: LDA / tetrahydrofuran / -78 °C

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

12: aq. NaOH / methanol / Ambient temperature

13: diethyl ether / 0 °C

With 1H-imidazole; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; dihydrogen peroxide; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1016/0040-4039(90)80021-D