(2R,3R)-2-((R)-1-Benzyloxy-ethyl)-3-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid

Base Information

Chemical Name:(2R,3R)-2-((R)-1-Benzyloxy-ethyl)-3-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid
CAS No.:149885-07-4
Molecular Formula:C₃₅H₄₇NO₆Si
Molecular Weight:605.847
Hs Code.:

Synonyms:(2R,3R)-2-((R)-1-Benzyloxy-ethyl)-3-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid

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Chemical Property of (2R,3R)-2-((R)-1-Benzyloxy-ethyl)-3-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid

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Technology Process of (2R,3R)-2-((R)-1-Benzyloxy-ethyl)-3-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid

There total 6 articles about (2R,3R)-2-((R)-1-Benzyloxy-ethyl)-3-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid 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: 71.0%

: 175656-29-8
{(1R,2R)-2-((R)-1-Benzyloxy-ethyl)-1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-but-3-ynyl}-carbamic acid tert-butyl ester

: 149885-07-4
(2R,3R)-2-((R)-1-Benzyloxy-ethyl)-3-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid

Guidance literature:: With sodium periodate; osmium(VIII) oxide;
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

: 149885-07-4
(2R,3R)-2-((R)-1-Benzyloxy-ethyl)-3-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid

Guidance literature:: Multi-step reaction with 3 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

With potassium hydroxide; sodium periodate; osmium(VIII) oxide; chloro-trimethyl-silane; diphenyl-phosphinic acid; triethylamine; In dichloromethane; 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

: 149885-07-4
(2R,3R)-2-((R)-1-Benzyloxy-ethyl)-3-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid

Guidance literature:: Multi-step reaction with 4 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

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