(R)-4-Benzyl-3-{(R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4R,5R)-1-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionyl}-oxazolidin-2-one

Base Information

• Chemical Name: (R)-4-Benzyl-3-{(R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4R,5R)-1-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionyl}-oxazolidin-2-one
• CAS No.: 211187-42-7
• Molecular Formula: C₅₂H₈₅NO₉Si₂
• Molecular Weight: 924.419

Synonyms:(R)-4-Benzyl-3-{(R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4R,5R)-1-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionyl}-oxazolidin-2-one

Chemical Property of (R)-4-Benzyl-3-{(R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4R,5R)-1-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionyl}-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (R)-4-Benzyl-3-{(R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4R,5R)-1-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionyl}-oxazolidin-2-one

There total 13 articles about (R)-4-Benzyl-3-{(R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4R,5R)-1-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionyl}-oxazolidin-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: 83.0%

t-butyldimethylsiyl triflate (69739-34-0) + (R)-4-Benzyl-3-[(R)-2-((2S,4S,5R,6S)-6-{(S)-2-[(R)-2-((1S,2R,3R,4R,5R)-1,3-dihydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexyl)-oxiranyl]-1-methyl-ethyl}-5-methyl-2-phenyl-[1,3]dioxan-4-yl)-propionyl]-oxazolidin-2-one (211187-40-5) → (R)-4-Benzyl-3-{(R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4R,5R)-1-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionyl}-oxazolidin-2-one (211187-42-7) + C52H85NO9Si2

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 19h;

DOI:10.1021/ja9806128

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (R)-4-Benzyl-3-{(R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4R,5R)-1-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionyl}-oxazolidin-2-one (211187-42-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 73 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -5 °C

2: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.67 h / Ambient temperature

3: 98 percent / 30percent aq. H₂O₂, 0.2 M aq. LiOH / tetrahydrofuran / 48 h / 0 °C

4: (COCl)2, DMF / benzene / 4 h / Ambient temperature

5: Pd₂(dba)3, i-Pr₂NEt / benzene / 0.5 h / Ambient temperature

6: 95 percent / HF*pyridine / tetrahydrofuran / 2.5 h / 0 °C

7: 86 percent / Zn(BH₄)2 / CH₂Cl₂; diethyl ether / a) -50 deg C, 15.5 h, b) 0 deg C, 1 h

8: 1 percent / t-BuOOH, VO(acac)2 / benzene; decane / 0.75 h / Ambient temperature

9: 83 percent / 2,6-lutidine / CH₂Cl₂ / 19 h / -78 °C

With 2,6-dimethylpyridine; tert.-butylhydroperoxide; lithium hydroxide; zinc(II) tetrahydroborate; oxalyl dichloride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; bis(acetylacetonate)oxovanadium; dihydrogen peroxide; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; In tetrahydrofuran; diethyl ether; decane; dichloromethane; benzene;

DOI:10.1021/ja9806128

Reference yield:

(R)-1-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-methylpentane-1,3-dione (101712-01-0,141423-22-5,141423-21-4) → (R)-4-Benzyl-3-{(R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4R,5R)-1-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionyl}-oxazolidin-2-one (211187-42-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) Sn(OTf)2, Et₃N / 1.) CH₂Cl₂, -20 deg C, 1 h, 2.) CH₂Cl₂, -78 deg C, 30 min

2: 100 percent / NaBH₄, AcOH / 0.25 h / Ambient temperature

3: 73 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -5 °C

4: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.67 h / Ambient temperature

5: 98 percent / 30percent aq. H₂O₂, 0.2 M aq. LiOH / tetrahydrofuran / 48 h / 0 °C

6: (COCl)2, DMF / benzene / 4 h / Ambient temperature

7: Pd₂(dba)3, i-Pr₂NEt / benzene / 0.5 h / Ambient temperature

8: 95 percent / HF*pyridine / tetrahydrofuran / 2.5 h / 0 °C

9: 86 percent / Zn(BH₄)2 / CH₂Cl₂; diethyl ether / a) -50 deg C, 15.5 h, b) 0 deg C, 1 h

10: 1 percent / t-BuOOH, VO(acac)2 / benzene; decane / 0.75 h / Ambient temperature

11: 83 percent / 2,6-lutidine / CH₂Cl₂ / 19 h / -78 °C

With 2,6-dimethylpyridine; tert.-butylhydroperoxide; lithium hydroxide; sodium tetrahydroborate; tin(II) trifluoromethanesulfonate; zinc(II) tetrahydroborate; oxalyl dichloride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; bis(acetylacetonate)oxovanadium; dihydrogen peroxide; pyridine hydrogenfluoride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; In tetrahydrofuran; diethyl ether; decane; dichloromethane; benzene;

DOI:10.1021/ja9806128

upstream raw materials:

t-butyldimethylsiyl triflate

(R)-4-Benzyl-3-[(R)-2-((2S,4S,5R,6S)-6-{(S)-2-[(R)-2-((1S,2R,3R,4R,5R)-1,3-dihydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexyl)-oxiranyl]-1-methyl-ethyl}-5-methyl-2-phenyl-[1,3]dioxan-4-yl)-propionyl]-oxazolidin-2-one

triisopropylsilyl trifluoromethanesulfonate

(R)-1-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-methylpentane-1,3-dione

Downstream raw materials:

(R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4S,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-3,5-dihydroxy-2,4-dimethyl-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionic acid

C₃₃H₅₄O₇Si

C₂₇H₃₈O₇

C₂₇H₄₀O₇

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