Acetic acid (2S,3R,4R,5R,6S)-4-acetoxy-2-[(R)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-1-((2S,3R)-3-hydroxy-2-methoxycarbonylamino-butyrylamino)-propoxy]-6-methyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Acetic acid (2S,3R,4R,5R,6S)-4-acetoxy-2-[(R)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-1-((2S,3R)-3-hydroxy-2-methoxycarbonylamino-butyrylamino)-propoxy]-6-methyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-3-yl ester
CAS No.:368835-97-6
Molecular Formula:C₃₈H₅₂Cl₃N₃O₁₄Si
Molecular Weight:909.287
Hs Code.:

Acetic acid (2S,3R,4R,5R,6S)-4-acetoxy-2-[(R)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-1-((2S,3R)-3-hydroxy-2-methoxycarbonylamino-butyrylamino)-propoxy]-6-methyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-3-yl ester

Synonyms:Acetic acid (2S,3R,4R,5R,6S)-4-acetoxy-2-[(R)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-1-((2S,3R)-3-hydroxy-2-methoxycarbonylamino-butyrylamino)-propoxy]-6-methyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-3-yl ester

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Chemical Property of Acetic acid (2S,3R,4R,5R,6S)-4-acetoxy-2-[(R)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-1-((2S,3R)-3-hydroxy-2-methoxycarbonylamino-butyrylamino)-propoxy]-6-methyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2S,3R,4R,5R,6S)-4-acetoxy-2-[(R)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-1-((2S,3R)-3-hydroxy-2-methoxycarbonylamino-butyrylamino)-propoxy]-6-methyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-3-yl ester

There total 13 articles about Acetic acid (2S,3R,4R,5R,6S)-4-acetoxy-2-[(R)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-1-((2S,3R)-3-hydroxy-2-methoxycarbonylamino-butyrylamino)-propoxy]-6-methyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-3-yl 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: 83.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: Acetic acid (2S,3R,4R,5R,6S)-3-acetoxy-2-[(R)-2,3-dihydroxy-1-((2S,3R)-3-hydroxy-2-methoxycarbonylamino-butyrylamino)-propoxy]-6-methyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester

: 368835-97-6
Acetic acid (2S,3R,4R,5R,6S)-4-acetoxy-2-[(R)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-1-((2S,3R)-3-hydroxy-2-methoxycarbonylamino-butyrylamino)-propoxy]-6-methyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-3-yl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 25 ℃; for 15h;
DOI:10.1021/ol0101178

Reference yield:

: 104198-85-8
O-<(tert-Butyl)dimethylsilyl>-N-(methoxycarbonyl)-L-threonin

: 368835-97-6
Acetic acid (2S,3R,4R,5R,6S)-4-acetoxy-2-[(R)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-1-((2S,3R)-3-hydroxy-2-methoxycarbonylamino-butyrylamino)-propoxy]-6-methyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: SOCl₂; pyridine / CH₂Cl₂ / 25 °C

2.1: silver oxide

2.2: Et₃N / 25 °C

3.1: NaBH₄ / ethanol / 0 °C

4.1: 100 percent / H₂ / Pd(OH)2 / ethanol / 25 °C

5.1: 40 percent / silver triflate / CH₂Cl₂ / -78 - 5 °C

6.1: 60 percent / 1N HCl / tetrahydrofuran / 9 h / 25 °C

7.1: 83 percent / imidazole / dimethylformamide / 15 h / 25 °C

With pyridine; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; thionyl chloride; hydrogen; silver trifluoromethanesulfonate; silver(l) oxide; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol0101178

Reference yield:

: [(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-chlorocarbonyl-propyl]-carbamic acid methyl ester

: 368835-97-6
Acetic acid (2S,3R,4R,5R,6S)-4-acetoxy-2-[(R)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-1-((2S,3R)-3-hydroxy-2-methoxycarbonylamino-butyrylamino)-propoxy]-6-methyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: silver oxide

1.2: Et₃N / 25 °C

2.1: NaBH₄ / ethanol / 0 °C

3.1: 100 percent / H₂ / Pd(OH)2 / ethanol / 25 °C

4.1: 40 percent / silver triflate / CH₂Cl₂ / -78 - 5 °C

5.1: 60 percent / 1N HCl / tetrahydrofuran / 9 h / 25 °C

6.1: 83 percent / imidazole / dimethylformamide / 15 h / 25 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; hydrogen; silver trifluoromethanesulfonate; silver(l) oxide; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol0101178