<5S-<5α(S^*),6β>>-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-5-<1-(phenylmethoxy)ethyl>-2-piperidinone

Base Information

• Chemical Name: <5S-<5α(S^*),6β>>-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-5-<1-(phenylmethoxy)ethyl>-2-piperidinone
• CAS No.: 91994-27-3
• Molecular Formula: C₃₂H₄₁NO₃Si
• Molecular Weight: 515.768

Synonyms:<5S-<5α(S^*),6β>>-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-5-<1-(phenylmethoxy)ethyl>-2-piperidinone

Chemical Property of <5S-<5α(S^*),6β>>-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-5-<1-(phenylmethoxy)ethyl>-2-piperidinone

Chemical Property:

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Technology Process of <5S-<5α(S^*),6β>>-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-5-<1-(phenylmethoxy)ethyl>-2-piperidinone

There total 2 articles about <5S-<5α(S^*),6β>>-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-5-<1-(phenylmethoxy)ethyl>-2-piperidinone 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: 82.0%

(2S,3R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-((R)-1-methyl-2-phenoxy-ethyl)-cyclopentanone oxime (91994-31-9) → <5S-<5α(S*),6β>>-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-5-<1-(phenylmethoxy)ethyl>-2-piperidinone (91994-27-3)

Guidance literature:

With dmap; p-toluenesulfonyl chloride; In pyridine; 1.) r.t., 30 min; 2.) 65 deg C, 3 h;

DOI:10.1021/ja00333a053

Reference yield:

(4R,5S)-4-((S)-1-Benzyloxy-ethyl)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-cyclopent-2-enone (91994-26-2) → <5S-<5α(S*),6β>>-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-5-<1-(phenylmethoxy)ethyl>-2-piperidinone (91994-27-3)

Guidance literature:

With hydroxylamine hydrochloride; sodium acetate; p-toluenesulfonyl chloride; 1-amino-3-(dimethylamino)propane; Yield given. Multistep reaction; 1.) EtOH, 42 h; 2.) pyridine, r.t. -> 65 deg C;

DOI:10.1021/ja00333a053

Reference yield:

<5S-<5α(S*),6β>>-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-5-<1-(phenylmethoxy)ethyl>-2-piperidinone (91994-27-3) → (R)-3-amino-2,3,4-trideoxy-5-O-<(1,1-dimethylethyl)diphenylsilyl>-2-<1-(phenylmethoxy)ethyl>-D-erythro-pentonic acid, β lactam (91994-33-1)

Guidance literature:

Multi-step reaction with 4 steps

2: 381 mg / potassium permanganate, sodium periodate, sodium bicarbonate / 2-methyl-propan-2-ol; H₂O / 1.5 h / Ambient temperature

3: 240 mg / 2 M sodium methoxide / methanol / 1.5 h / 0 °C

4: 2.) triethylamine; 3.) dicyclohexylcarbodiimide / 1.) trifluoroacetic acid, 0 deg C, 20 min; 2.) acetonitrile, 5 min; 3.) 65 deg C, 5 h

With potassium permanganate; sodium periodate; sodium methylate; sodium hydrogencarbonate; triethylamine; dicyclohexyl-carbodiimide; In methanol; water; tert-butyl alcohol;

DOI:10.1021/ja00333a053

upstream raw materials:

(4R,5S)-4-((S)-1-Benzyloxy-ethyl)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-cyclopent-2-enone

(2S,3R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-((R)-1-methyl-2-phenoxy-ethyl)-cyclopentanone oxime

Downstream raw materials:

1,1-dimethylethyl <2R-<2a,3β(R^*)>>-2-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-3,6-dihydro-6-oxo-3-<1-(phenylmethoxy)ethyl>-1-(2H)-piperidinecarboxylate

(R)-3-amino-2,3,4-trideoxy-5-O-<(1,1-dimethylethyl)diphenylsilyl>-2-<1-(phenylmethoxy)ethyl>-D-erythro-pentonic acid, β lactam

(R)-2,3,4-trideoxy-3-<<(1,1-dimethylethoxy)carbonyl>amino>-5-O-<(1,1-dimethylethyl)diphenylsilyl>-2-<1-(phenylmethoxy)ethyl>-D-erythropentanoic acid

(2S,3R)-2-((S)-1-Benzyloxy-ethyl)-3-(tert-butoxycarbonyl-oxalyl-amino)-5-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid

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