(3R,4R)-3-((R)-1-Benzyloxy-ethyl)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-azetidin-2-one

Base Information

Chemical Name:(3R,4R)-3-((R)-1-Benzyloxy-ethyl)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-azetidin-2-one
CAS No.:149885-08-5
Molecular Formula:C₃₀H₃₇NO₃Si
Molecular Weight:487.714
Hs Code.:

Synonyms:(3R,4R)-3-((R)-1-Benzyloxy-ethyl)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-azetidin-2-one

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Chemical Property of (3R,4R)-3-((R)-1-Benzyloxy-ethyl)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-azetidin-2-one

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Technology Process of (3R,4R)-3-((R)-1-Benzyloxy-ethyl)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-azetidin-2-one

There total 8 articles about (3R,4R)-3-((R)-1-Benzyloxy-ethyl)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-azetidin-2-one 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:

: 1027868-85-4
(2R,3R)-3-Amino-2-((R)-1-benzyloxy-ethyl)-5-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid

: 149885-08-5
(3R,4R)-3-((R)-1-Benzyloxy-ethyl)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-azetidin-2-one

Guidance literature:: With dicyclohexyl-carbodiimide; Yield given;
DOI:10.1016/S0040-4039(00)77631-3

Reference yield:

: 149837-00-3
(2R,3S)-3-((R)-1-Benzyloxy-ethyl)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-pent-4-ynoic acid

: 149885-08-5
(3R,4R)-3-((R)-1-Benzyloxy-ethyl)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-azetidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: DPPA, Et₃N / benzene / 3.5 h / Heating

2: TMSCl / CH₂Cl₂ / 16 h / Ambient temperature

3: 1.) OsO₄, NaIO₄, 2.) KOH, NaIO₄ / 1.) THF, H₂O, rt, 6 d, 2.) THF, H₂O, rt, 1.5 h

4: H₂O / trifluoroacetic acid / 0.33 h / 0 °C

5: dicyclohexylcarbodiimide, Et₃N / acetonitrile / 10 h / 65 - 68 °C

With potassium hydroxide; sodium periodate; osmium(VIII) oxide; chloro-trimethyl-silane; diphenyl-phosphinic acid; water; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; acetonitrile; trifluoroacetic acid; benzene;
DOI:10.1021/jo952092u

Reference yield:

: 149836-98-6
(4S,5R)-3-{(2R,3S)-3-((R)-1-Benzyloxy-ethyl)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-trimethylsilanyl-pent-4-ynoyl}-4-methyl-5-phenyl-oxazolidin-2-one

: 149885-08-5
(3R,4R)-3-((R)-1-Benzyloxy-ethyl)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-azetidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 74 percent / LiOH*H₂O, H₂O₂ / H₂O; tetrahydrofuran; dimethylformamide / Ambient temperature

2: DPPA, Et₃N / benzene / 3.5 h / Heating

3: TMSCl / CH₂Cl₂ / 16 h / Ambient temperature

4: 1.) OsO₄, NaIO₄, 2.) KOH, NaIO₄ / 1.) THF, H₂O, rt, 6 d, 2.) THF, H₂O, rt, 1.5 h

5: H₂O / trifluoroacetic acid / 0.33 h / 0 °C

6: dicyclohexylcarbodiimide, Et₃N / acetonitrile / 10 h / 65 - 68 °C

With potassium hydroxide; lithium hydroxide; sodium periodate; osmium(VIII) oxide; chloro-trimethyl-silane; diphenyl-phosphinic acid; water; dihydrogen peroxide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; trifluoroacetic acid; benzene;
DOI:10.1021/jo952092u