dimethyl (5R,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-5-ethyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylate

Base Information

Chemical Name:dimethyl (5R,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-5-ethyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylate
CAS No.:442202-14-4
Molecular Formula:C₂₈H₃₇NO₅Si
Molecular Weight:495.691
Hs Code.:

Synonyms:dimethyl (5R,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-5-ethyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylate

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Chemical Property of dimethyl (5R,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-5-ethyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylate

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Technology Process of dimethyl (5R,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-5-ethyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylate

There total 15 articles about dimethyl (5R,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-5-ethyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylate 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: 75.0%

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 442202-28-0
methyl (2S,3R)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-3-ethyl-6-trifluoromethanesulfonyloxy-3,4-dihydro-2H-pyridine-1-carboxylate

: 442202-14-4
dimethyl (5R,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-5-ethyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylate

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In N,N-dimethyl-formamide; at 70 ℃; for 14h;
DOI:10.1016/j.tet.2004.05.039

Reference yield:

: 117935-51-0
(R)-1-O-acetyl-2-ethyl-1,3-propanediol

: 442202-14-4
dimethyl (5R,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-5-ethyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylate

Guidance literature:: Multi-step reaction with 15 steps

1.1: PPTS / CH₂Cl₂ / 2 h / 20 °C

2.1: K₂CO₃ / methanol / 3 h / 20 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

4.2: 695 mg / tetrahydrofuran; hexane / 1.5 h / 20 °C

5.1: 80 percent / (DHQD)2PYR; K₂OsO₄*2H₂O; K₃Fe(CN)6 / K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 24 h / 0 °C

6.1: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 20 h / 20 °C

7.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

8.1: 1.3 g / NaN₃ / dimethylformamide / 15 h / 80 °C

9.1: PPTS / ethanol / 2 h / 60 °C

10.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

11.1: NaH / tetrahydrofuran / 0.25 h / 0 °C

11.2: 935 mg / tetrahydrofuran / 2 h / 20 °C

12.1: 73 percent / H₂ / Pd-C / ethyl acetate / 72 h / 3040 Torr

13.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

13.2: 97 percent / tetrahydrofuran; hexane / 1 h / -78 - 0 °C

14.1: hexamethyldisilazane; n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

14.2: 97 percent / tetrahydrofuran; hexane / 1 h / -78 - -45 °C

15.1: 75 percent / Pd(Ph₃P)4; Et₃N / dimethylformamide / 14 h / 70 °C

With dmap; potassium osmate(VI); tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; sodium azide; oxalyl dichloride; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; potassium hexacyanoferrate(III); palladium on activated charcoal; potassium carbonate; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 3.1: Swern oxidation / 4.2: Wittig reaction / 10.1: Swern oxidation / 11.2: Horner-Emmons reaction;
DOI:10.1016/j.tet.2004.05.039

Reference yield:

: 442202-32-6
(2S)-2-(2-ethylbut-3-enyloxy)tetrahydropyrane

: 442202-14-4
dimethyl (5R,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-5-ethyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylate

Guidance literature:: Multi-step reaction with 11 steps

1.1: 80 percent / (DHQD)2PYR; K₂OsO₄*2H₂O; K₃Fe(CN)6 / K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 24 h / 0 °C

2.1: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 20 h / 20 °C

3.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

4.1: 1.3 g / NaN₃ / dimethylformamide / 15 h / 80 °C

5.1: PPTS / ethanol / 2 h / 60 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

7.1: NaH / tetrahydrofuran / 0.25 h / 0 °C

7.2: 935 mg / tetrahydrofuran / 2 h / 20 °C

8.1: 73 percent / H₂ / Pd-C / ethyl acetate / 72 h / 3040 Torr

9.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

9.2: 97 percent / tetrahydrofuran; hexane / 1 h / -78 - 0 °C

10.1: hexamethyldisilazane; n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

10.2: 97 percent / tetrahydrofuran; hexane / 1 h / -78 - -45 °C

11.1: 75 percent / Pd(Ph₃P)4; Et₃N / dimethylformamide / 14 h / 70 °C

With dmap; potassium osmate(VI); tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; sodium azide; oxalyl dichloride; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; potassium hexacyanoferrate(III); palladium on activated charcoal; potassium carbonate; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 6.1: Swern oxidation / 7.2: Horner-Emmons reaction;
DOI:10.1016/j.tet.2004.05.039